Angucyclines: Total syntheses, new structures, and biosynthetic studies of an emerging new class of antibiotics

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Bioorganic Chemistry Deoxysugars, Polyketides and Related Classes: Synthesis, Biosynthesis, Enzymes

Part of the book series: Topics in Current Chemistry ((4143,volume 188))

Abstract

General and recent aspects of chemical syntheses on angucyclinones and selected related natural products are summarized here. In the first part of this review on angucyclines, the chemical reaction used as a key step for the construction of the angucyclinone frame is discussed. In the second part, new members of the angucycline group of antibiotics, their bioactivity and recent biosynthetic studies including modern aspects of molecular biology (genetics) are reviewed.

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References

  1. Begley S (1994) Newsweek March 28:39

    Google Scholar 

  2. Drautz H, Zähner H, Rohr J, Zeeck A (1986) J Antibiot 39:1657

    CAS  Google Scholar 

  3. Rohr J, Thiericke R (1992) Nat Prod Rep 9:103

    Article  CAS  Google Scholar 

  4. Thomson RH (1987) Naturally Occurring Quinones III. Recent Advances. Chapman and Hall, London

    Google Scholar 

  5. Oka M, Konishi M, Oki T, Ohashi M (1990) Tetrahedron Lett 31:7473

    Article  CAS  Google Scholar 

  6. Oka M, Kamel H, Hamagishi Y, Tomita K, Miyaki T, Konishi M, Oki T (1990) J Antibiot 43:967

    CAS  Google Scholar 

  7. Kunstmann MP, Mitscher LA (1966) J Org Chem 31:2920

    Article  Google Scholar 

  8. Dann M, Lefemine DV, Barbatschi F, Shu P, Kunstmann MP, Mitscher LA, Bohonos N (1965) Antimicrob Agents Chemother 1965:832

    Google Scholar 

  9. Ayukawa S, Takeuchi T, Sezaki M, Hara T, Umezawa H, Nagatsu T (1968) J Antibiot 21:350

    CAS  Google Scholar 

  10. Sato Y, Gould SJ (1986) J Am Chem Soc 108:4625

    Article  CAS  Google Scholar 

  11. Rohr JA, Zeeck, Floss HG (1988) J Antibiot 41:126

    CAS  Google Scholar 

  12. Rohr J, Zeeck A (1987) J Antibiot 40:459

    CAS  Google Scholar 

  13. Ohta K, Mizuta E, Okazaki H, Kishi T (1984) Chem Pharm Bull 32:4350

    CAS  Google Scholar 

  14. Kawashima A, Yoshimura Y, Goto J, Nakaike S, Mizutani T, Handa K, Omura S (1988) J Antibiot 41:1913

    CAS  Google Scholar 

  15. Sawada Y, Numata KI, Murakami T, Tanimichi H, Yamamoto S, Oki T (1990) J Antibiot 43:715

    CAS  Google Scholar 

  16. Kakushima M, Nishio M, Numata KI, Konishi M, Oki T (1990) J Antibiot 43:1028

    CAS  Google Scholar 

  17. Tsunakawa M, Nishio M, Ohkuma H, Tsuno T, Konishi M, Naito T, Oki T, Kawaguchi H (1989) J Org Chem 54:2532

    Article  CAS  Google Scholar 

  18. Brown PM, Thomson RH (1976) J Chem Soc, Perkin Trans 1 1976: 997

    Article  Google Scholar 

  19. Jacobsen N, Torsell K (1973) Acta Chem Scand 27:3211

    Article  CAS  Google Scholar 

  20. Sutherland JK, Towers P (1981) J Chem Soc, Chem Commun 1981:740

    Article  Google Scholar 

  21. Krohn K (1990) Tetrahedron 46:291

    Article  CAS  Google Scholar 

  22. Krohn K, Müller U, Priyono W, Sarstedt B, Stoffregen A (1984) Liebigs Ann Chem 1984:306

    Article  Google Scholar 

  23. Krohn K, Dröge W, Hintze F (1995) Annal Quim 91:388

    CAS  Google Scholar 

  24. Arsenault G, Broadbent AD, Hutten-Czapski P (1983) J Chem Soc, Chem Commun 1983:437

    Article  Google Scholar 

  25. Ashcroft AE, Davies DT, Sutherland JK (1984) Tetrahedron 40:4579

    Article  CAS  Google Scholar 

  26. Ahmed Z, Cava MP (1981) Tetrahedron Lett 22:5239

    Article  CAS  Google Scholar 

  27. Cava MP, Ahmed Z, Benfaremo N, Murphy Jr. RA, O’Malley GJ (1984) Tetrahedron 40:4767

    Article  CAS  Google Scholar 

  28. Krohn K, Bakus W (1986) Synthesis 1986:942

    Article  Google Scholar 

  29. Krohn K, Priyono W (1986) Angew Chem 98:338

    Article  CAS  Google Scholar 

  30. Krohn K (1979) J Chem Res (S) 1979:318

    Google Scholar 

  31. Kraus GA, Wu Y (1991) Tetrahedron Lett 32:3803

    Article  CAS  Google Scholar 

  32. Kraus GA, Wu Y (1995) Annal Quim 91:393

    Google Scholar 

  33. Fumagalli SE, Eugster CH (1971) Helv Chim Acta 54:959

    Article  CAS  Google Scholar 

  34. Marschalk C, Koenig F, Ouroussoff N (1936) Bull Soc Chim F 3:1545

    CAS  Google Scholar 

  35. Krohn K, Sarsted B (1983) Angew Chem 95:897

    Article  CAS  Google Scholar 

  36. Krohn K, Baltus W (1982) Liebigs Ann Chem 1982:1579

    Article  Google Scholar 

  37. Krohn K, Ballwanz F, Baltus W (1993) Liebigs Ann Chem 1993:911

    Article  Google Scholar 

  38. Lakshmikantham MV, Ravichandran K, Gosciniak DJ, Cava MP (1985) Tetrahedron Lett 26:4703

    Article  CAS  Google Scholar 

  39. Krohn K, Khanbabaee K, Flörke U, Jones PG, Chrapkowski A (1994) Liebigs Ann Chem 1994:471

    Article  Google Scholar 

  40. Gerken M, Blank S, Kolar C, Hermentin P (1989) J Carbohydr Chem 8:247

    Article  CAS  Google Scholar 

  41. Yates P, Mackay AC, Garneau FX (1968) Tetrahedron Lett 1968:5389

    Article  Google Scholar 

  42. Garcia-Garibay MA, Gamarnik A, Pang L, Jenks WS (1994) J Am Chem Soc 116:12095

    Article  CAS  Google Scholar 

  43. Bowie JH, Johnson AW (1967) Tetrahedron Lett 1967:1449

    Article  Google Scholar 

  44. Maehr H, Liu C-M, Liu M, Perrotta A, Smallheer JM, Williams T, Blount JF (1982) J Antibiot 35:1627

    CAS  Google Scholar 

  45. Katsuura K, Snieckus V (1985) Tetrahedron Lett 26:9

    Article  CAS  Google Scholar 

  46. Katsuura K, Snieckus V (1987) Can J Chem 65:124

    Article  CAS  Google Scholar 

  47. Valderrama JA, Araya-Maturana R, González MF, Tapia R, Farina F, Paredes MC (1991) J Chem Soc, Perkin Trans 1 1991:555

    Article  Google Scholar 

  48. Uemura M, Take K, Hayashi Y (1983) J Chem Soc, Chem Commun 1983:858

    Article  Google Scholar 

  49. Uemura M, Take K, Isobe K, Minami T, Hayashi Y (1985) Tetrahedron 41:5771

    Article  CAS  Google Scholar 

  50. Carothers WH, Coffman DD (1932) J Am Chem Soc 54:4071

    Article  CAS  Google Scholar 

  51. Tomaszewski JE, Manning WB, Muschik GM (1977) Tetrahedron Lett 1977:971

    Article  Google Scholar 

  52. Manning WB (1981) Tetrahedron Lett 22:1571

    Article  CAS  Google Scholar 

  53. Guingant A, Barreto MM (1987) Tetrahedron Lett 28:3107

    Article  CAS  Google Scholar 

  54. Gould SJ, Cheng X-C, Melville C (1994) J Am Chem Soc 116:1800

    Article  CAS  Google Scholar 

  55. Krohn K (1986) Angew Chem 98:788

    Article  CAS  Google Scholar 

  56. Stowell JC (1979) Carbanions in Organic Synthesis. Wiley Interscience, New York, p 37

    Google Scholar 

  57. Valderrama JA, Pessoa-Mahana CD, Tapia R (1994) J Chem Soc, Perkin Trans 1 1994:3521

    Article  Google Scholar 

  58. Matsumoto T, Sohma T, Yamaguchi H, Kurata S, Suzuki K (1995) Synlett 1995:263

    Article  Google Scholar 

  59. Matsumoto T, Sohma T, Yamaguchi H, Kurata S, Suzuki K (1995) Tetrahedron 51:7347

    Article  CAS  Google Scholar 

  60. Tochtermann W, Malchow A, Timm H (1978) Chem Ber 111:1233

    Article  CAS  Google Scholar 

  61. Bridson JN, Bennett SM, Butler G (1980) J Chem Soc, Chem Commun 1980:413

    Article  Google Scholar 

  62. Larsen DS, O’shea MD (1993) Tetrahedron Lett 34:1373

    Article  CAS  Google Scholar 

  63. Larsen DS, O’shea MD (1993) Tetrahedron Lett 34:3769

    Article  CAS  Google Scholar 

  64. Larsen DS, OÇShea MD (1995) J Chem Soc, Chem Commun 1995:1019

    Google Scholar 

  65. Sezaki M, Kondo S, Maeda K, Umezawa H (1970) Tetrahedron 26:5171

    Article  CAS  Google Scholar 

  66. Larsen DS, OÇShea MD, Brooker S (1996) J Chem Soc, Chem Commun 1996:203

    Google Scholar 

  67. Kelly TR, Whiting A, Chandrakumar NS (1986) J Am Chem Soc 108:3510

    Article  CAS  Google Scholar 

  68. Krohn K, Khanbabaee K (1994) Angew Chem 106:100

    Article  CAS  Google Scholar 

  69. Fleming I, Henning R, Plaut H (1984) J Chem Soc, Chem Commun 1984:29

    Article  Google Scholar 

  70. Still WC (1976) J Org Chem 41:3063

    Article  CAS  Google Scholar 

  71. Hudrlik PF, Hudrlik AM, Nagendrappa G, Yimenu T, Zellers ET, Chin E (1980) J Am Chem Soc 102:6896

    Article  Google Scholar 

  72. Chan TH, Nwe KT (1992) J Org Chem 57:6107

    Article  CAS  Google Scholar 

  73. Krohn K, Khanbabaee K (1994) Liebigs Ann Chem 1994:1109

    Article  Google Scholar 

  74. Krohn K, Khanbabaee K, Micheel J (1995) Liebigs Ann Chem 1995:1529

    Article  Google Scholar 

  75. Micheel J (1995) Diploma thesis. Universität Paderborn

    Google Scholar 

  76. Matsuo G, Miki Y, Nakata M, Matsumura S, Toshima K (1996) J Chem Soc, Chem Commun 1996:225

    Google Scholar 

  77. Gilpin ML, Balchin J, Box SJ, Tyler JW (1989) J Antibiot 42:627

    CAS  Google Scholar 

  78. Krohn K (1980) Tetrahedron Lett 21:3557

    Article  CAS  Google Scholar 

  79. Laatsch H (1985) Liebigs Ann Chem 1985:251

    Article  Google Scholar 

  80. Boeckman Jr. RK, Delton MH, Dolak TM, Watanabe T, Glick MD (1979) J Org Chem 44:4396

    Article  CAS  Google Scholar 

  81. Rozeboom MD, Tegmo-Larsson I-M, Houk KN (1981) J Org Chem 46:2338

    Article  CAS  Google Scholar 

  82. Krohn K, Khanbabaee K, Jones PG (1995) Liebigs Ann Chem 1995:1981

    Article  Google Scholar 

  83. Kim K, Reibenspies J, Sulikowski G (1992) J Org Chem 57:5557

    Article  CAS  Google Scholar 

  84. Kim K, Guo Y, Sulikowski, G. A. (1995) J Org Chem 60:6866

    Article  CAS  Google Scholar 

  85. Boyd VA, Reibenspies J, Sulikowski GA (1995) Tetrahedron Lett 36:4001

    Article  CAS  Google Scholar 

  86. Krohn K, Böker N, Freund C (1996) J Org Chem 1996 (in preparation)

    Google Scholar 

  87. Boyd VA, Sulikowski GA (1995) J Am Chem Soc 117:8472

    Article  CAS  Google Scholar 

  88. Billen G, Scholl KU, Stroech KD, Steglich W (1988) In: HEJ Atta-ur-Rahman (eds) Natural Products Chemistry. Springer, Heidelberg, p 305

    Google Scholar 

  89. Kim K, Sulikowski, G.A. (1995) Angew Chem 107:2587

    Article  Google Scholar 

  90. Sasaki T, Yoshida J, Itoh M, Gomi S, Shomura T, Sezaki M (1988) J Antibiot 41:835

    CAS  Google Scholar 

  91. Sasaki T, Gomi S, Sezaki M, Takeuchi Y, Kodoma Y, Kawamura K(1988) J Antibiot 41:843

    CAS  Google Scholar 

  92. Kraus G, Zhao G (1995) Synlett 1995:541

    Article  Google Scholar 

  93. Kraus G, Zhao G (1996) J Org Chem 61:2770

    Article  CAS  Google Scholar 

  94. Nicolas TE, Franck RW (1995) J Org Chem 60:6904

    Article  CAS  Google Scholar 

  95. Rohr J (1992) J Org Chem 57:5217

    Article  CAS  Google Scholar 

  96. Gould SJ, Halley KA (1991) J Am Chem Soc 113:5092

    Article  CAS  Google Scholar 

  97. Yamaguchi M, Okuma T, Horiguchi A, Ikeura C, Minami T (1992) J Org Chem 57:1647

    Article  CAS  Google Scholar 

  98. Yamaguchi M, Hasebe K, Higashi H, Uchida M, Irie A, Minami T (1990) J Org Chem 55:1611

    Article  CAS  Google Scholar 

  99. Harris TM, Harris CM, Hindley KB (1974) Fortschr Chem Org Naturstoff 31:217

    CAS  Google Scholar 

  100. Krohn K, Roemer E, Top M, Wagner C (1993) Angew Chem 105:1220

    Article  CAS  Google Scholar 

  101. Krohn K, Schäfer G (1996) Liebigs Ann Chem 1996:265

    Google Scholar 

  102. Krohn K, Roemer E, Top M (1996) Liebigs Ann Chem 1996:271

    Google Scholar 

  103. Grunwell JR, Heinzman SW (1980) Tetrahedron Lett 21:4305

    Article  Google Scholar 

  104. Wurm G, Geres U (1984) Arch Pharm (Weinheim) 317:606

    Article  CAS  Google Scholar 

  105. Wurm G, Gurka H-J (1986) Arch Pharm (Weinheim) 319:190

    Article  CAS  Google Scholar 

  106. Stille JK, Groh BL (1987) J Am Chem soc 109:813

    Article  CAS  Google Scholar 

  107. Stille JK (1986) Angew Chem, Int Ed Engl 25:508

    Article  Google Scholar 

  108. Tamayo N, Echavarren AM, Paredes MC, Farina F, Noheda P (1990) Tetrahedron Lett 31:5189

    Article  CAS  Google Scholar 

  109. Mata EG, Mascaretti OA (1988) Tetrahedron Lett 29:6893

    Article  CAS  Google Scholar 

  110. Krohn K (1989) Building blocks for the total synthesis of anthracyclinones. In: W Herz; H Grisebach; GW Kirby; Ch Tamm (eds) Prog Chem Org Nat Prod. Springer, Wien, New York, p 37

    Google Scholar 

  111. Chuang C-P, Wang S-F (1994) Tetrahedron Lett 35:4365

    Article  CAS  Google Scholar 

  112. Gordon DM, Danishefsky SJ, Schulte GK (1992) J Org Chem 57:7052

    Article  CAS  Google Scholar 

  113. Dötz KH, Popall M, Müller G (1985) J Organomet Chem 291:C1

    Article  Google Scholar 

  114. Wulff WD, Xu Y-C (1988) J Am Chem Soc 110:2312

    Article  CAS  Google Scholar 

  115. Oki T, Konishi M, Tomatsu K, Tomita K, Saitoh KI, Tsunakawa M, Nishio M, Miyaki T, Kawaguchi H (1988) J Antibiot 41:1701

    CAS  Google Scholar 

  116. Tomita K, Nishio M, Saitoh K, Yamamoto H, Hoshino Y, Ohkuma H, Konishi M, Miyaki T, Oki T (1990) J Antibiot 43:755

    CAS  Google Scholar 

  117. Oki T, Kakushima M, Nishio M, Kamel H, Hirano M, Swada Y, Konishi M (1990) J Antibiot 43:1230

    CAS  Google Scholar 

  118. Oki T, Tenmyo O, Hirano M, Tomatsu K, Kamai H (1990) J Antibiot 43:763

    CAS  Google Scholar 

  119. Kakushima M, Masuyoshi S, Hirano M, Shinoda M, Ohta A, Kamei H, Oki T (1991) Antimicrob Agents Chemother 35:2185

    CAS  Google Scholar 

  120. Oki T, Kakushima M, Hirano M, Takahashi A, Ohta A, Masuyoshi S, Hatori M, Kamei H (1992) J Antibiot 45:1512

    CAS  Google Scholar 

  121. Oki T (1991) Recent progress in antifungal chemotherapy. In: H Yamaguchi, GS Kobayashi, H Takahashi (eds) Marcel Dekker; New York, p 381

    Google Scholar 

  122. Gerber NN, Lechevalier MP (1984) Can J Chem 62:2818

    Article  CAS  Google Scholar 

  123. Rickards RW (1989) J Antibiot 42:336

    CAS  Google Scholar 

  124. Kelly TR, Li Q, Bhushan V (1990) Tetrahedron Lett 31:161

    Article  CAS  Google Scholar 

  125. Kelly TR, Xu W, Ma Z, Li Q, Bushan V (1993) J Am Chem Soc 115:5843

    Article  CAS  Google Scholar 

  126. Hauser FM, Caringal Y (1990) J Org Chem 55:555

    Article  CAS  Google Scholar 

  127. Yamaguchi M, Okuma T, Ikeura C, Minami T (1992) J Chem Soc, Chem Commun 1992:434

    Article  Google Scholar 

  128. Daves GD, Jr (1990) Acc Chem Res 23:201

    Article  CAS  Google Scholar 

  129. Jamarillo C, Knapp S (1993) Synthesis 1993

    Google Scholar 

  130. Suzuki K, Matsumoto T (1993) Total synthesis of Aryl C-glycoside antibiotics. In: G Lukacs (ed) Recent progress in the chemical synthesis of antibiotics and related microbial products. Springer, Berlin, Heidelberg, New York, p 353

    Google Scholar 

  131. Kwok D-I, Outten RO, Huhn R, Daves GD, Jr. (1988) J Org Chem 53:5359

    Article  CAS  Google Scholar 

  132. Outten RA, Daves GD (1989) J Org Chem 54:29

    Article  CAS  Google Scholar 

  133. Matsumoto T, Hosoya T, Suzuki K (1991) Synlett 1991:709

    Google Scholar 

  134. Matsumoto T, Hosoya T, Suzuki K (1992) J Am Chem Soc 114:3568

    Article  CAS  Google Scholar 

  135. Tius MC, Gu X, Gomez-Galeno G (1990) J Am Chem Soc 112:8188

    Article  CAS  Google Scholar 

  136. Tius MA, Gomez-Galeno J, Gu X-q, Zaidi JH (1991) J Am Chem Soc 113:5775

    Article  CAS  Google Scholar 

  137. Boyd VA, Drake BE, Sulikowski GA (1993) J Org Chem 58:3191

    Article  CAS  Google Scholar 

  138. Arhart RJ, Martin JC (1972) J Am Chem Soc 94:5003

    Article  CAS  Google Scholar 

  139. Andrews FL, Larsen DS (1994) Tetrahedron Lett 35:8693

    Article  CAS  Google Scholar 

  140. Brinkman LC, Ley FR, Seaton PJ (1993) J Nat Prod 56:374

    Article  CAS  Google Scholar 

  141. Okabe T, Ogino H, Suzuki H, Suda AOH (06.11.92) Jpn Kokai Tokkyo Koho 04, 316, 492 [92, 316, 492]; CA 118:167614v

    Google Scholar 

  142. Hayakawa Y, Ha S-C, Kim YJ, Furihata K, Seto H (1991) J Antibiot 44:1179

    CAS  Google Scholar 

  143. Seto H, Hayakawa Y, Shimazu A (23.10.1992) Jpn. Kokai Tokkyo Koho 04, 300, 849 [92, 300, 849]; CA 118:146245k

    Google Scholar 

  144. Fujioka K, Furihata K, Shimazu A, Hayakawa Y, Seto H (1991) J Antibiot 44:1025

    CAS  Google Scholar 

  145. Seto H, Hayakawa Y, Shimazu A, Furuhata K, Fujioka K (02.06.1992) JP 04,159,291 [92, 159, 291] CA 117: 232216n

    Google Scholar 

  146. Lazhko El, Novozhenov MY, Malanicheva IA (1992) Bioorg Khim 18:1519

    CAS  Google Scholar 

  147. Weber S, Zolke C, Rohr J, Beale JM (1994) J Org Chem 59:4211

    Article  CAS  Google Scholar 

  148. Henkel T, Rohr J, Beale JM, Schwenen L (1990) J Antibiot 43:492

    CAS  Google Scholar 

  149. Maul C, Zerlin M, Wohlert S-E, Rohr J (1996) unpublished results

    Google Scholar 

  150. Kanamura T, Nozaki Y, Muroi M (29.11.1990) JP 02,289,532 [90, 289, 532] CA 115:47759 n

    Google Scholar 

  151. Igarashi M, Sasao C, Yoshida A, Naganawa H, Hamada M, Takeuchi T (1995) J Antibiot 48:335

    CAS  Google Scholar 

  152. Senda S, Seto H (27.12. 1989) Eur Pat Appl EP 435, 221 CA 115:112826 y

    Google Scholar 

  153. Ritzau M (1992) Dissertation, Universität Göttingen

    Google Scholar 

  154. Tanaka Y, Sugoh M, Yoshida H, Arai N, Shiomi K, Matsumoto A, Takahashi Y, Omura S (1995) J Antibiot 48:1525

    CAS  Google Scholar 

  155. Gerlitz M, Udvarnoki G, Rohr J (1995) GIT Fachz Lab 39:888

    CAS  Google Scholar 

  156. Gerlitz M, Udvarnoki G, Rohr J (1995) Angew Chem Int Ed Engl 34:1617

    Article  CAS  Google Scholar 

  157. Gerlitz M (1995) Dissertation, Universität Göttingen, Cuvillier, Göttingen

    Google Scholar 

  158. Phife DW, Patton RW, Berrie RL, Yarborough R, Puar MS, Patel M, Bishop WR, Coval SJ (1995) Tetrahedron Lett 36:6995

    Article  CAS  Google Scholar 

  159. Wege D (1996) Aust J Chem 49:669

    CAS  Google Scholar 

  160. Gould SJ, Cheng XC (1994) J Org Chem 59:400

    Article  CAS  Google Scholar 

  161. Miyata S, Ohhata N, H, Murai, Masui Y, Ezaki M, Takase S, Nishikawa M, Kiyoto S, Okuhara M, Kohsaka M (1992) J Antibiot 45:1029

    CAS  Google Scholar 

  162. Miyata S, Hashimoto M, Fujie K, Shouho M, Sogabe K, Kiyoto S, Okuhara M, Kohsaka M (1992) J Antibiot 45:1041

    CAS  Google Scholar 

  163. Oohata N, Motoaki N, Kiyoto S, Takase S, Hemmi K, Murai H, Okuhara M (30.6.1989) Eur. Pat Appl EP 405,421 CA 115:157125k

    Google Scholar 

  164. Etoh H, Iguchi M, Nagasawa T, Tani Y, Yamada H, Fukami H (1987) Agric Biol Chem 51:1819

    CAS  Google Scholar 

  165. Rohr J, Schönewolf M, Udvarnoki G, Eckardt K, Schumann G, Wagner C, Beale JM, Sorey SD (1993) J Org Chem 58:2547

    Article  CAS  Google Scholar 

  166. Bindseil KU, Hug P, Peter HH, Petersen F, Roggo BE (1995) J Antibiot 48:457

    CAS  Google Scholar 

  167. Bethe B (1994), Dissertation, Universität Göttingen, Cuviller, Göttingen

    Google Scholar 

  168. Chu M, Yarborough R, Schwartz J, Patel MG, Horan AC, Gullo VP, Das PR, Puar MS (1993) J Antibiot 46:861

    CAS  Google Scholar 

  169. Okabe T, Funaishi K, Hagiwara M, Kawamura K, Suda H, Sato F, Okanishi M (03.12. 1990) JP 02, 291, 287 [90, 291, 287] CA 115: 69926s

    Google Scholar 

  170. Imamura N, Kakinuma K, Ikekawa N, Tanaka H, Omura S (1981) J Antibiot 34:1517

    CAS  Google Scholar 

  171. Kawamura N, Sawa R, Takahashi Y, Sawa T, Kinoshita N, Naganawa H, Hamada M, Takeuchi T (1995) J Antibiot 48:1521

    CAS  Google Scholar 

  172. Sawa R, Matsuda N, Uchida T, Ikeda T, Sawa T, Naganawa H, Hamada M, Takeuchi T (1991) J Antibiot 44:396

    CAS  Google Scholar 

  173. Ojiri K, Suda H, Okura A, Kawamura K, Okanishi M (08.02.91) JP 0330,687 [91, 30, 687] CA 115:157135p

    Google Scholar 

  174. Kawashima A, Maejima A, Miyoshi T, Tamai M, Hanada K, Omura S (22.01. 1990) JP 03,220,196 [91, 220, 196] CA 116:104492s

    Google Scholar 

  175. Müller H, Fugmann B, Weber K, Schmidt D (1991) Dechema/GDCh-. Symposium: “Neue niedermolekulare Naturstoffe und Perspektiven für ihre Anwendung”, Irsee/Bayern, 13.2.-15.2.1991

    Google Scholar 

  176. Kawashima A, Hamaguchi T, Amaka T, Hanada K (1992) JP 04,178,379, CA 118:21058v

    Google Scholar 

  177. Umezawa H, Takeuchi T, Sawa T, Hamada M, Naganawa H, Uchida T, Imoto M (1991) EP 191-399-B

    Google Scholar 

  178. Mithani S, Weeratunga G, Taylor NJ, Dmitrienko GI (1994) J Am Chem Soc 116:2209

    Article  CAS  Google Scholar 

  179. Gould SJ, Tamayo N, Melville CR, Cone MC (1994) J Am Chem Soc 116:2207

    Article  CAS  Google Scholar 

  180. Seaton PJ, Gould SJ (1987) J Am Chem Soc 109:5282

    Article  CAS  Google Scholar 

  181. Smitka TA, Bonjouklian R, Perun JTJ, Hunt AH, Foster RS, Mynderse JS, Yao RC (1992) J Antibiot 45:581

    CAS  Google Scholar 

  182. Lin H-C, Chang S-C, Wang N-L, Chang I-R (1994) J Antibiot 47:675

    CAS  Google Scholar 

  183. Young J-J, Ho S-N, Ju W-M, Chang I-R (1994) J Antibiot 47:681

    CAS  Google Scholar 

  184. Cone MC, Melville CR, Gore MP, Gould SJ (1993) J Org Chem 58:1058

    Article  CAS  Google Scholar 

  185. Gould SJ, Melville CR (1995) Bioorganic Med Chem Lett 6:51

    Article  Google Scholar 

  186. Aoyama T, Zhao W, Kojima F, Muraoka, Y, Naganawa H, Takeuchi T, Aoyagi, T (1993) J Antibiot 46:1471

    CAS  Google Scholar 

  187. Seto H, Hayakawa Y, Shimazu A (1993) JP 05, 85, 998 [93 85, 998],CA 119:70550d

    Google Scholar 

  188. Shin-ya K, Furihata K, Teshima Y (1992) Tetrahedron Lett 33:7025

    Article  CAS  Google Scholar 

  189. Volkmann C, Rössner E, Metzler M, Zähner H, Zeeck A (1995) Liebigs Ann Chem 1995:1169

    Article  Google Scholar 

  190. Weissinger M, Bockholt H, Rohr J (1996) unpublished

    Google Scholar 

  191. Bockholt H, Udvarnoki G, Rohr J, Mocek U, Beale JM, Floss HG (1994) J Org Chem 59:2064

    Article  CAS  Google Scholar 

  192. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) Science 262:1546

    Article  CAS  Google Scholar 

  193. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1995) Nature 375:549

    Article  CAS  Google Scholar 

  194. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) J Am Chem Soc 115:11671

    Article  CAS  Google Scholar 

  195. Shen B, Summers RG, Wendt-Pienkowski E, Hutchinson CR (1995) J Am Chem Soc 117:6811

    Article  CAS  Google Scholar 

  196. Rohr J (1995) Angew Chem Int Ed Engl 34:881

    Article  CAS  Google Scholar 

  197. Ayer SW, McInnes AG, Thibault P, Walter JA, Doull JL, Parnell T, Vining LC (1991) Tetrahedron Lett 32:6301

    Article  CAS  Google Scholar 

  198. Doull JL, Ayer SW, Singh AK, Thibault P (1993) J Antibiot 46:869

    CAS  Google Scholar 

  199. Han L, Yang K, Ramalingam E, Mosher RH, Vining LC (1994) Microbiology 140:3379

    CAS  Google Scholar 

  200. Seaton PJ, Gould SJ (1988) J Am Chem Soc 110:5912

    Article  CAS  Google Scholar 

  201. Cone MC, Hassan AM, Gore MP, Gould SJ, Borders DB, Alluri MR (1994) J Org Chem 59:1923

    Article  CAS  Google Scholar 

  202. Yang K, Han L, Ayer SW, Vining LC (1996) Microbiology 142:123

    CAS  Google Scholar 

  203. O’Hagan D (1991) The polyketide metabolites. Ellis Horwood, New York

    Google Scholar 

  204. O’Hagan D (1995) Nat Prod Rep 12:1

    Article  CAS  Google Scholar 

  205. Hutchinson CR, Fujii I (1995) Annu Rev Microbiol 49:201

    Article  CAS  Google Scholar 

  206. Tsuda M, Sato H, Tanaka Y, Yazawa K, Mikami Y, Sasaki T, Kobayashi J (1996) J Chem Soc Perkin Trans 1:773

    Google Scholar 

  207. Udvarnoki G, Henkel T, Machinek R, Rohr J (1992) J Org Chem 57:1274

    Article  CAS  Google Scholar 

  208. Gould SJ, Cheng X-C, Halley KR (1992) J Am Chem Soc 114:10066

    Article  CAS  Google Scholar 

  209. Gould SJ, Cheng X-C (1993) Tetrahedron 49:11135

    Article  CAS  Google Scholar 

  210. Weibbach U (1996) Diplomarbeit, Universität Göttingen

    Google Scholar 

  211. Bechthold A (1996) private communication

    Google Scholar 

  212. Donadio S, Staver MJ, McAlpine JB, Swanson SJ, Katz L (1991) Science 252:675

    Article  CAS  Google Scholar 

  213. Cortes J, Haydock SF, Roberts GA, Bevitt DB, Leadlay PF (1990) Nature 348:176

    Article  CAS  Google Scholar 

  214. Leadlay PF, Staunton J, Aparicio JF, Bevitt DJ, Caffrey P, Cortes J, Marsden A, Roberts GA (1993) Biochem Soc Trans 21:218

    CAS  Google Scholar 

  215. Anderson JA, Lin B-K, Williams H-J, Scott AI (1988) J Am Chem Soc 110:1623

    Article  CAS  Google Scholar 

  216. Erickson WR, Gould SJ (1985) J Am Chem Soc 107:5831

    Article  CAS  Google Scholar 

  217. Gould SJ, Cheng X-C (1993) Tetrahedron 49:11135

    Article  CAS  Google Scholar 

  218. Decker H, Haag S (1995) J Bacteriol 177:6126

    CAS  Google Scholar 

  219. Decker H, Rohr J, Motamedi H, Zähner H, Hutchinson CR (1995) Gene 166:121

    Article  CAS  Google Scholar 

  220. Decker H, Haag S, Udvarnoki G, Rohr J (1995) Angew Chem Int Ed Engl 34:1107

    Article  CAS  Google Scholar 

  221. Decker H, Gaisser S, Pelzer S, Schneider P, Westrich L, Wohlleben W, Bechthold A (1996) FEMS Lett, in press

    Google Scholar 

  222. Beninga C, Wohlert S-E, Rohr J (1996) unpublished results

    Google Scholar 

  223. Beninga C (1994) Diplomarbeit, Universität Göttingen

    Google Scholar 

  224. Wohlert S-E (1994) Diplomarbeit, Universität Göttingen

    Google Scholar 

  225. Polishchuk L, Stefanishin EE, Dekhtyarenko TD, Sten’ko AS, Zaverukha VB, Matselyukh BP (1987) Mikrobiol Z (Ukr) 49:24

    CAS  Google Scholar 

  226. Zaverukha VB, Polevoda BV, Polishchuk LV, Matselyukh BP (1992) Mikrobiol Z (Ukr) 54:30

    CAS  Google Scholar 

  227. Matselyukh B, Polishchuk L, Weibbach U, Wohlert S-E, Rohr J (1996) J Antibiot, in preparation

    Google Scholar 

  228. Cone MC, Melville CR, Carney JR, Gore MP, Gould SJ (1995) Tetrahedron 51:3095

    Article  CAS  Google Scholar 

  229. Carter GT, Fantini AA, James JC, Borders DB, White RJ (1984) Tetrahedron Lett 25:255

    Article  CAS  Google Scholar 

  230. Elespuru RK, Gonda SK (1984) Science 223:69

    Article  CAS  Google Scholar 

  231. Morimoto M, Okubo S, Tomita F, Marumo H (1981) J Antibiot 34:701

    CAS  Google Scholar 

  232. Takahashi K, Tomita F (1983) J Antibiot 36:1531

    CAS  Google Scholar 

  233. Carter GT, Fantini AA, James JC, Borders DB, White RJ (1985) J Antibiot 38:242

    CAS  Google Scholar 

  234. Misra R, Tritch HR, Pandey RC (1985) J Antibiot 38:1280

    CAS  Google Scholar 

  235. Keyes RF, Kingston DGI (1989) J Org Chem 54:6127

    Article  CAS  Google Scholar 

  236. Eguchi T, Li H-Y, Kazami J-I, Kakinuma K, Otake N (1990) J Antibiot 43:1077

    CAS  Google Scholar 

  237. Balitz DM, O’Herron FA, Bush J, Vyas DM, Nettleton DE, Grulich RE, Bradner WT, Doyle TW, Arnold E, Clardy J (1981) J Antibiot 34:1544

    CAS  Google Scholar 

  238. Hatano K, Higashide E, Shibata M, Kameda Y, Horii S (19801) Agric Biol Chem 44:1157

    CAS  Google Scholar 

  239. McGee LR, Misra R (1990) J Am Chem Soc 112:2386

    Article  CAS  Google Scholar 

  240. Nakajima S, Kojiri K, Suda H, Okanishi M (1991) J Antibiot 44:1061

    CAS  Google Scholar 

  241. Kojiri K, Arakawa H, Satoh F, Kawamura K, Okura A, Suda H, Okanishi M (1991) J Antibiot 44:1054

    CAS  Google Scholar 

  242. Kikuchi O, Eguchi T, Kakinuma K, Koezuka Y, Shindo K, Otake N (1993) J Antibiot 46:985

    CAS  Google Scholar 

  243. Hosoya T, Takashiro E, Matsumoto T, Suzuki K (1994) J Am Chem Soc 116:1004

    Article  CAS  Google Scholar 

  244. Farr RN, Kwok DI, Daves J GD (1992) J Org Chem 57:2093

    Article  CAS  Google Scholar 

  245. Shen B, Hutchinson CR (1994) J Bacteriol 269:30726

    CAS  Google Scholar 

  246. Decker H, Motamedi H, Hutchinson CR (1993) J Bacteriol 175:3876

    CAS  Google Scholar 

  247. Udvarnoki G, Wagner C, Machinek R, Rohr J (1995) Angew Chem Int Ed Engl 34:565

    Article  CAS  Google Scholar 

  248. Cane DE (1994) Science 263:338

    Article  CAS  Google Scholar 

  249. Piepersberg W (1994) Critical Rev Biotechnol 14:251

    Article  CAS  Google Scholar 

  250. Tsoi CJ, Khosla C (1995) Chemistry & Biology 2:355

    Article  CAS  Google Scholar 

  251. Katz L, Donadio S (1993) Annu Rev Microbiol 47:875

    Article  CAS  Google Scholar 

  252. Fu H, Hopwood DA, Khosla C (1994) Chemistry & Biology 1:205

    Article  CAS  Google Scholar 

  253. Rouhi M (1995) C & EN 1995:9

    Google Scholar 

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Krohn, K., Rohr, J. (1997). Angucyclines: Total syntheses, new structures, and biosynthetic studies of an emerging new class of antibiotics. In: Rohr, J. (eds) Bioorganic Chemistry Deoxysugars, Polyketides and Related Classes: Synthesis, Biosynthesis, Enzymes. Topics in Current Chemistry, vol 188. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119236

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