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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Begley S (1994) Newsweek March 28:39
Drautz H, Zähner H, Rohr J, Zeeck A (1986) J Antibiot 39:1657
Rohr J, Thiericke R (1992) Nat Prod Rep 9:103
Thomson RH (1987) Naturally Occurring Quinones III. Recent Advances. Chapman and Hall, London
Oka M, Konishi M, Oki T, Ohashi M (1990) Tetrahedron Lett 31:7473
Oka M, Kamel H, Hamagishi Y, Tomita K, Miyaki T, Konishi M, Oki T (1990) J Antibiot 43:967
Kunstmann MP, Mitscher LA (1966) J Org Chem 31:2920
Dann M, Lefemine DV, Barbatschi F, Shu P, Kunstmann MP, Mitscher LA, Bohonos N (1965) Antimicrob Agents Chemother 1965:832
Ayukawa S, Takeuchi T, Sezaki M, Hara T, Umezawa H, Nagatsu T (1968) J Antibiot 21:350
Sato Y, Gould SJ (1986) J Am Chem Soc 108:4625
Rohr JA, Zeeck, Floss HG (1988) J Antibiot 41:126
Rohr J, Zeeck A (1987) J Antibiot 40:459
Ohta K, Mizuta E, Okazaki H, Kishi T (1984) Chem Pharm Bull 32:4350
Kawashima A, Yoshimura Y, Goto J, Nakaike S, Mizutani T, Handa K, Omura S (1988) J Antibiot 41:1913
Sawada Y, Numata KI, Murakami T, Tanimichi H, Yamamoto S, Oki T (1990) J Antibiot 43:715
Kakushima M, Nishio M, Numata KI, Konishi M, Oki T (1990) J Antibiot 43:1028
Tsunakawa M, Nishio M, Ohkuma H, Tsuno T, Konishi M, Naito T, Oki T, Kawaguchi H (1989) J Org Chem 54:2532
Brown PM, Thomson RH (1976) J Chem Soc, Perkin Trans 1 1976: 997
Jacobsen N, Torsell K (1973) Acta Chem Scand 27:3211
Sutherland JK, Towers P (1981) J Chem Soc, Chem Commun 1981:740
Krohn K (1990) Tetrahedron 46:291
Krohn K, Müller U, Priyono W, Sarstedt B, Stoffregen A (1984) Liebigs Ann Chem 1984:306
Krohn K, Dröge W, Hintze F (1995) Annal Quim 91:388
Arsenault G, Broadbent AD, Hutten-Czapski P (1983) J Chem Soc, Chem Commun 1983:437
Ashcroft AE, Davies DT, Sutherland JK (1984) Tetrahedron 40:4579
Ahmed Z, Cava MP (1981) Tetrahedron Lett 22:5239
Cava MP, Ahmed Z, Benfaremo N, Murphy Jr. RA, O’Malley GJ (1984) Tetrahedron 40:4767
Krohn K, Bakus W (1986) Synthesis 1986:942
Krohn K, Priyono W (1986) Angew Chem 98:338
Krohn K (1979) J Chem Res (S) 1979:318
Kraus GA, Wu Y (1991) Tetrahedron Lett 32:3803
Kraus GA, Wu Y (1995) Annal Quim 91:393
Fumagalli SE, Eugster CH (1971) Helv Chim Acta 54:959
Marschalk C, Koenig F, Ouroussoff N (1936) Bull Soc Chim F 3:1545
Krohn K, Sarsted B (1983) Angew Chem 95:897
Krohn K, Baltus W (1982) Liebigs Ann Chem 1982:1579
Krohn K, Ballwanz F, Baltus W (1993) Liebigs Ann Chem 1993:911
Lakshmikantham MV, Ravichandran K, Gosciniak DJ, Cava MP (1985) Tetrahedron Lett 26:4703
Krohn K, Khanbabaee K, Flörke U, Jones PG, Chrapkowski A (1994) Liebigs Ann Chem 1994:471
Gerken M, Blank S, Kolar C, Hermentin P (1989) J Carbohydr Chem 8:247
Yates P, Mackay AC, Garneau FX (1968) Tetrahedron Lett 1968:5389
Garcia-Garibay MA, Gamarnik A, Pang L, Jenks WS (1994) J Am Chem Soc 116:12095
Bowie JH, Johnson AW (1967) Tetrahedron Lett 1967:1449
Maehr H, Liu C-M, Liu M, Perrotta A, Smallheer JM, Williams T, Blount JF (1982) J Antibiot 35:1627
Katsuura K, Snieckus V (1985) Tetrahedron Lett 26:9
Katsuura K, Snieckus V (1987) Can J Chem 65:124
Valderrama JA, Araya-Maturana R, González MF, Tapia R, Farina F, Paredes MC (1991) J Chem Soc, Perkin Trans 1 1991:555
Uemura M, Take K, Hayashi Y (1983) J Chem Soc, Chem Commun 1983:858
Uemura M, Take K, Isobe K, Minami T, Hayashi Y (1985) Tetrahedron 41:5771
Carothers WH, Coffman DD (1932) J Am Chem Soc 54:4071
Tomaszewski JE, Manning WB, Muschik GM (1977) Tetrahedron Lett 1977:971
Manning WB (1981) Tetrahedron Lett 22:1571
Guingant A, Barreto MM (1987) Tetrahedron Lett 28:3107
Gould SJ, Cheng X-C, Melville C (1994) J Am Chem Soc 116:1800
Krohn K (1986) Angew Chem 98:788
Stowell JC (1979) Carbanions in Organic Synthesis. Wiley Interscience, New York, p 37
Valderrama JA, Pessoa-Mahana CD, Tapia R (1994) J Chem Soc, Perkin Trans 1 1994:3521
Matsumoto T, Sohma T, Yamaguchi H, Kurata S, Suzuki K (1995) Synlett 1995:263
Matsumoto T, Sohma T, Yamaguchi H, Kurata S, Suzuki K (1995) Tetrahedron 51:7347
Tochtermann W, Malchow A, Timm H (1978) Chem Ber 111:1233
Bridson JN, Bennett SM, Butler G (1980) J Chem Soc, Chem Commun 1980:413
Larsen DS, O’shea MD (1993) Tetrahedron Lett 34:1373
Larsen DS, O’shea MD (1993) Tetrahedron Lett 34:3769
Larsen DS, OÇShea MD (1995) J Chem Soc, Chem Commun 1995:1019
Sezaki M, Kondo S, Maeda K, Umezawa H (1970) Tetrahedron 26:5171
Larsen DS, OÇShea MD, Brooker S (1996) J Chem Soc, Chem Commun 1996:203
Kelly TR, Whiting A, Chandrakumar NS (1986) J Am Chem Soc 108:3510
Krohn K, Khanbabaee K (1994) Angew Chem 106:100
Fleming I, Henning R, Plaut H (1984) J Chem Soc, Chem Commun 1984:29
Still WC (1976) J Org Chem 41:3063
Hudrlik PF, Hudrlik AM, Nagendrappa G, Yimenu T, Zellers ET, Chin E (1980) J Am Chem Soc 102:6896
Chan TH, Nwe KT (1992) J Org Chem 57:6107
Krohn K, Khanbabaee K (1994) Liebigs Ann Chem 1994:1109
Krohn K, Khanbabaee K, Micheel J (1995) Liebigs Ann Chem 1995:1529
Micheel J (1995) Diploma thesis. Universität Paderborn
Matsuo G, Miki Y, Nakata M, Matsumura S, Toshima K (1996) J Chem Soc, Chem Commun 1996:225
Gilpin ML, Balchin J, Box SJ, Tyler JW (1989) J Antibiot 42:627
Krohn K (1980) Tetrahedron Lett 21:3557
Laatsch H (1985) Liebigs Ann Chem 1985:251
Boeckman Jr. RK, Delton MH, Dolak TM, Watanabe T, Glick MD (1979) J Org Chem 44:4396
Rozeboom MD, Tegmo-Larsson I-M, Houk KN (1981) J Org Chem 46:2338
Krohn K, Khanbabaee K, Jones PG (1995) Liebigs Ann Chem 1995:1981
Kim K, Reibenspies J, Sulikowski G (1992) J Org Chem 57:5557
Kim K, Guo Y, Sulikowski, G. A. (1995) J Org Chem 60:6866
Boyd VA, Reibenspies J, Sulikowski GA (1995) Tetrahedron Lett 36:4001
Krohn K, Böker N, Freund C (1996) J Org Chem 1996 (in preparation)
Boyd VA, Sulikowski GA (1995) J Am Chem Soc 117:8472
Billen G, Scholl KU, Stroech KD, Steglich W (1988) In: HEJ Atta-ur-Rahman (eds) Natural Products Chemistry. Springer, Heidelberg, p 305
Kim K, Sulikowski, G.A. (1995) Angew Chem 107:2587
Sasaki T, Yoshida J, Itoh M, Gomi S, Shomura T, Sezaki M (1988) J Antibiot 41:835
Sasaki T, Gomi S, Sezaki M, Takeuchi Y, Kodoma Y, Kawamura K(1988) J Antibiot 41:843
Kraus G, Zhao G (1995) Synlett 1995:541
Kraus G, Zhao G (1996) J Org Chem 61:2770
Nicolas TE, Franck RW (1995) J Org Chem 60:6904
Rohr J (1992) J Org Chem 57:5217
Gould SJ, Halley KA (1991) J Am Chem Soc 113:5092
Yamaguchi M, Okuma T, Horiguchi A, Ikeura C, Minami T (1992) J Org Chem 57:1647
Yamaguchi M, Hasebe K, Higashi H, Uchida M, Irie A, Minami T (1990) J Org Chem 55:1611
Harris TM, Harris CM, Hindley KB (1974) Fortschr Chem Org Naturstoff 31:217
Krohn K, Roemer E, Top M, Wagner C (1993) Angew Chem 105:1220
Krohn K, Schäfer G (1996) Liebigs Ann Chem 1996:265
Krohn K, Roemer E, Top M (1996) Liebigs Ann Chem 1996:271
Grunwell JR, Heinzman SW (1980) Tetrahedron Lett 21:4305
Wurm G, Geres U (1984) Arch Pharm (Weinheim) 317:606
Wurm G, Gurka H-J (1986) Arch Pharm (Weinheim) 319:190
Stille JK, Groh BL (1987) J Am Chem soc 109:813
Stille JK (1986) Angew Chem, Int Ed Engl 25:508
Tamayo N, Echavarren AM, Paredes MC, Farina F, Noheda P (1990) Tetrahedron Lett 31:5189
Mata EG, Mascaretti OA (1988) Tetrahedron Lett 29:6893
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
Chuang C-P, Wang S-F (1994) Tetrahedron Lett 35:4365
Gordon DM, Danishefsky SJ, Schulte GK (1992) J Org Chem 57:7052
Dötz KH, Popall M, Müller G (1985) J Organomet Chem 291:C1
Wulff WD, Xu Y-C (1988) J Am Chem Soc 110:2312
Oki T, Konishi M, Tomatsu K, Tomita K, Saitoh KI, Tsunakawa M, Nishio M, Miyaki T, Kawaguchi H (1988) J Antibiot 41:1701
Tomita K, Nishio M, Saitoh K, Yamamoto H, Hoshino Y, Ohkuma H, Konishi M, Miyaki T, Oki T (1990) J Antibiot 43:755
Oki T, Kakushima M, Nishio M, Kamel H, Hirano M, Swada Y, Konishi M (1990) J Antibiot 43:1230
Oki T, Tenmyo O, Hirano M, Tomatsu K, Kamai H (1990) J Antibiot 43:763
Kakushima M, Masuyoshi S, Hirano M, Shinoda M, Ohta A, Kamei H, Oki T (1991) Antimicrob Agents Chemother 35:2185
Oki T, Kakushima M, Hirano M, Takahashi A, Ohta A, Masuyoshi S, Hatori M, Kamei H (1992) J Antibiot 45:1512
Oki T (1991) Recent progress in antifungal chemotherapy. In: H Yamaguchi, GS Kobayashi, H Takahashi (eds) Marcel Dekker; New York, p 381
Gerber NN, Lechevalier MP (1984) Can J Chem 62:2818
Rickards RW (1989) J Antibiot 42:336
Kelly TR, Li Q, Bhushan V (1990) Tetrahedron Lett 31:161
Kelly TR, Xu W, Ma Z, Li Q, Bushan V (1993) J Am Chem Soc 115:5843
Hauser FM, Caringal Y (1990) J Org Chem 55:555
Yamaguchi M, Okuma T, Ikeura C, Minami T (1992) J Chem Soc, Chem Commun 1992:434
Daves GD, Jr (1990) Acc Chem Res 23:201
Jamarillo C, Knapp S (1993) Synthesis 1993
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
Kwok D-I, Outten RO, Huhn R, Daves GD, Jr. (1988) J Org Chem 53:5359
Outten RA, Daves GD (1989) J Org Chem 54:29
Matsumoto T, Hosoya T, Suzuki K (1991) Synlett 1991:709
Matsumoto T, Hosoya T, Suzuki K (1992) J Am Chem Soc 114:3568
Tius MC, Gu X, Gomez-Galeno G (1990) J Am Chem Soc 112:8188
Tius MA, Gomez-Galeno J, Gu X-q, Zaidi JH (1991) J Am Chem Soc 113:5775
Boyd VA, Drake BE, Sulikowski GA (1993) J Org Chem 58:3191
Arhart RJ, Martin JC (1972) J Am Chem Soc 94:5003
Andrews FL, Larsen DS (1994) Tetrahedron Lett 35:8693
Brinkman LC, Ley FR, Seaton PJ (1993) J Nat Prod 56:374
Okabe T, Ogino H, Suzuki H, Suda AOH (06.11.92) Jpn Kokai Tokkyo Koho 04, 316, 492 [92, 316, 492]; CA 118:167614v
Hayakawa Y, Ha S-C, Kim YJ, Furihata K, Seto H (1991) J Antibiot 44:1179
Seto H, Hayakawa Y, Shimazu A (23.10.1992) Jpn. Kokai Tokkyo Koho 04, 300, 849 [92, 300, 849]; CA 118:146245k
Fujioka K, Furihata K, Shimazu A, Hayakawa Y, Seto H (1991) J Antibiot 44:1025
Seto H, Hayakawa Y, Shimazu A, Furuhata K, Fujioka K (02.06.1992) JP 04,159,291 [92, 159, 291] CA 117: 232216n
Lazhko El, Novozhenov MY, Malanicheva IA (1992) Bioorg Khim 18:1519
Weber S, Zolke C, Rohr J, Beale JM (1994) J Org Chem 59:4211
Henkel T, Rohr J, Beale JM, Schwenen L (1990) J Antibiot 43:492
Maul C, Zerlin M, Wohlert S-E, Rohr J (1996) unpublished results
Kanamura T, Nozaki Y, Muroi M (29.11.1990) JP 02,289,532 [90, 289, 532] CA 115:47759 n
Igarashi M, Sasao C, Yoshida A, Naganawa H, Hamada M, Takeuchi T (1995) J Antibiot 48:335
Senda S, Seto H (27.12. 1989) Eur Pat Appl EP 435, 221 CA 115:112826 y
Ritzau M (1992) Dissertation, Universität Göttingen
Tanaka Y, Sugoh M, Yoshida H, Arai N, Shiomi K, Matsumoto A, Takahashi Y, Omura S (1995) J Antibiot 48:1525
Gerlitz M, Udvarnoki G, Rohr J (1995) GIT Fachz Lab 39:888
Gerlitz M, Udvarnoki G, Rohr J (1995) Angew Chem Int Ed Engl 34:1617
Gerlitz M (1995) Dissertation, Universität Göttingen, Cuvillier, Göttingen
Phife DW, Patton RW, Berrie RL, Yarborough R, Puar MS, Patel M, Bishop WR, Coval SJ (1995) Tetrahedron Lett 36:6995
Wege D (1996) Aust J Chem 49:669
Gould SJ, Cheng XC (1994) J Org Chem 59:400
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
Miyata S, Hashimoto M, Fujie K, Shouho M, Sogabe K, Kiyoto S, Okuhara M, Kohsaka M (1992) J Antibiot 45:1041
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
Etoh H, Iguchi M, Nagasawa T, Tani Y, Yamada H, Fukami H (1987) Agric Biol Chem 51:1819
Rohr J, Schönewolf M, Udvarnoki G, Eckardt K, Schumann G, Wagner C, Beale JM, Sorey SD (1993) J Org Chem 58:2547
Bindseil KU, Hug P, Peter HH, Petersen F, Roggo BE (1995) J Antibiot 48:457
Bethe B (1994), Dissertation, Universität Göttingen, Cuviller, Göttingen
Chu M, Yarborough R, Schwartz J, Patel MG, Horan AC, Gullo VP, Das PR, Puar MS (1993) J Antibiot 46:861
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
Imamura N, Kakinuma K, Ikekawa N, Tanaka H, Omura S (1981) J Antibiot 34:1517
Kawamura N, Sawa R, Takahashi Y, Sawa T, Kinoshita N, Naganawa H, Hamada M, Takeuchi T (1995) J Antibiot 48:1521
Sawa R, Matsuda N, Uchida T, Ikeda T, Sawa T, Naganawa H, Hamada M, Takeuchi T (1991) J Antibiot 44:396
Ojiri K, Suda H, Okura A, Kawamura K, Okanishi M (08.02.91) JP 0330,687 [91, 30, 687] CA 115:157135p
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
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
Kawashima A, Hamaguchi T, Amaka T, Hanada K (1992) JP 04,178,379, CA 118:21058v
Umezawa H, Takeuchi T, Sawa T, Hamada M, Naganawa H, Uchida T, Imoto M (1991) EP 191-399-B
Mithani S, Weeratunga G, Taylor NJ, Dmitrienko GI (1994) J Am Chem Soc 116:2209
Gould SJ, Tamayo N, Melville CR, Cone MC (1994) J Am Chem Soc 116:2207
Seaton PJ, Gould SJ (1987) J Am Chem Soc 109:5282
Smitka TA, Bonjouklian R, Perun JTJ, Hunt AH, Foster RS, Mynderse JS, Yao RC (1992) J Antibiot 45:581
Lin H-C, Chang S-C, Wang N-L, Chang I-R (1994) J Antibiot 47:675
Young J-J, Ho S-N, Ju W-M, Chang I-R (1994) J Antibiot 47:681
Cone MC, Melville CR, Gore MP, Gould SJ (1993) J Org Chem 58:1058
Gould SJ, Melville CR (1995) Bioorganic Med Chem Lett 6:51
Aoyama T, Zhao W, Kojima F, Muraoka, Y, Naganawa H, Takeuchi T, Aoyagi, T (1993) J Antibiot 46:1471
Seto H, Hayakawa Y, Shimazu A (1993) JP 05, 85, 998 [93 85, 998],CA 119:70550d
Shin-ya K, Furihata K, Teshima Y (1992) Tetrahedron Lett 33:7025
Volkmann C, Rössner E, Metzler M, Zähner H, Zeeck A (1995) Liebigs Ann Chem 1995:1169
Weissinger M, Bockholt H, Rohr J (1996) unpublished
Bockholt H, Udvarnoki G, Rohr J, Mocek U, Beale JM, Floss HG (1994) J Org Chem 59:2064
McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) Science 262:1546
McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1995) Nature 375:549
McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) J Am Chem Soc 115:11671
Shen B, Summers RG, Wendt-Pienkowski E, Hutchinson CR (1995) J Am Chem Soc 117:6811
Rohr J (1995) Angew Chem Int Ed Engl 34:881
Ayer SW, McInnes AG, Thibault P, Walter JA, Doull JL, Parnell T, Vining LC (1991) Tetrahedron Lett 32:6301
Doull JL, Ayer SW, Singh AK, Thibault P (1993) J Antibiot 46:869
Han L, Yang K, Ramalingam E, Mosher RH, Vining LC (1994) Microbiology 140:3379
Seaton PJ, Gould SJ (1988) J Am Chem Soc 110:5912
Cone MC, Hassan AM, Gore MP, Gould SJ, Borders DB, Alluri MR (1994) J Org Chem 59:1923
Yang K, Han L, Ayer SW, Vining LC (1996) Microbiology 142:123
O’Hagan D (1991) The polyketide metabolites. Ellis Horwood, New York
O’Hagan D (1995) Nat Prod Rep 12:1
Hutchinson CR, Fujii I (1995) Annu Rev Microbiol 49:201
Tsuda M, Sato H, Tanaka Y, Yazawa K, Mikami Y, Sasaki T, Kobayashi J (1996) J Chem Soc Perkin Trans 1:773
Udvarnoki G, Henkel T, Machinek R, Rohr J (1992) J Org Chem 57:1274
Gould SJ, Cheng X-C, Halley KR (1992) J Am Chem Soc 114:10066
Gould SJ, Cheng X-C (1993) Tetrahedron 49:11135
Weibbach U (1996) Diplomarbeit, Universität Göttingen
Bechthold A (1996) private communication
Donadio S, Staver MJ, McAlpine JB, Swanson SJ, Katz L (1991) Science 252:675
Cortes J, Haydock SF, Roberts GA, Bevitt DB, Leadlay PF (1990) Nature 348:176
Leadlay PF, Staunton J, Aparicio JF, Bevitt DJ, Caffrey P, Cortes J, Marsden A, Roberts GA (1993) Biochem Soc Trans 21:218
Anderson JA, Lin B-K, Williams H-J, Scott AI (1988) J Am Chem Soc 110:1623
Erickson WR, Gould SJ (1985) J Am Chem Soc 107:5831
Gould SJ, Cheng X-C (1993) Tetrahedron 49:11135
Decker H, Haag S (1995) J Bacteriol 177:6126
Decker H, Rohr J, Motamedi H, Zähner H, Hutchinson CR (1995) Gene 166:121
Decker H, Haag S, Udvarnoki G, Rohr J (1995) Angew Chem Int Ed Engl 34:1107
Decker H, Gaisser S, Pelzer S, Schneider P, Westrich L, Wohlleben W, Bechthold A (1996) FEMS Lett, in press
Beninga C, Wohlert S-E, Rohr J (1996) unpublished results
Beninga C (1994) Diplomarbeit, Universität Göttingen
Wohlert S-E (1994) Diplomarbeit, Universität Göttingen
Polishchuk L, Stefanishin EE, Dekhtyarenko TD, Sten’ko AS, Zaverukha VB, Matselyukh BP (1987) Mikrobiol Z (Ukr) 49:24
Zaverukha VB, Polevoda BV, Polishchuk LV, Matselyukh BP (1992) Mikrobiol Z (Ukr) 54:30
Matselyukh B, Polishchuk L, Weibbach U, Wohlert S-E, Rohr J (1996) J Antibiot, in preparation
Cone MC, Melville CR, Carney JR, Gore MP, Gould SJ (1995) Tetrahedron 51:3095
Carter GT, Fantini AA, James JC, Borders DB, White RJ (1984) Tetrahedron Lett 25:255
Elespuru RK, Gonda SK (1984) Science 223:69
Morimoto M, Okubo S, Tomita F, Marumo H (1981) J Antibiot 34:701
Takahashi K, Tomita F (1983) J Antibiot 36:1531
Carter GT, Fantini AA, James JC, Borders DB, White RJ (1985) J Antibiot 38:242
Misra R, Tritch HR, Pandey RC (1985) J Antibiot 38:1280
Keyes RF, Kingston DGI (1989) J Org Chem 54:6127
Eguchi T, Li H-Y, Kazami J-I, Kakinuma K, Otake N (1990) J Antibiot 43:1077
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
Hatano K, Higashide E, Shibata M, Kameda Y, Horii S (19801) Agric Biol Chem 44:1157
McGee LR, Misra R (1990) J Am Chem Soc 112:2386
Nakajima S, Kojiri K, Suda H, Okanishi M (1991) J Antibiot 44:1061
Kojiri K, Arakawa H, Satoh F, Kawamura K, Okura A, Suda H, Okanishi M (1991) J Antibiot 44:1054
Kikuchi O, Eguchi T, Kakinuma K, Koezuka Y, Shindo K, Otake N (1993) J Antibiot 46:985
Hosoya T, Takashiro E, Matsumoto T, Suzuki K (1994) J Am Chem Soc 116:1004
Farr RN, Kwok DI, Daves J GD (1992) J Org Chem 57:2093
Shen B, Hutchinson CR (1994) J Bacteriol 269:30726
Decker H, Motamedi H, Hutchinson CR (1993) J Bacteriol 175:3876
Udvarnoki G, Wagner C, Machinek R, Rohr J (1995) Angew Chem Int Ed Engl 34:565
Cane DE (1994) Science 263:338
Piepersberg W (1994) Critical Rev Biotechnol 14:251
Tsoi CJ, Khosla C (1995) Chemistry & Biology 2:355
Katz L, Donadio S (1993) Annu Rev Microbiol 47:875
Fu H, Hopwood DA, Khosla C (1994) Chemistry & Biology 1:205
Rouhi M (1995) C & EN 1995:9
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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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