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Collective Synthesis of Monoterpenoid Indole Alkaloids Using Bioinspired Strategies

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Abstract

In recent years, collective total synthesis, in which natural products are synthesized exhaustively from common intermediates, has attracted attention in academia and industry. In this chapter, collective total syntheses of monoterpenoid indole alkaloids found in higher plants are highlighted. Secologanin and strictosidine, which are key branching intermediates in biosynthesis, were synthesized in gram-scale quantities. Then, 18 indole alkaloid syntheses from secologanin tetraacetate or its aglycones were accomplished. These total syntheses, using bioinspired strategies reminiscent of a tree diagram, can provide several different skeletal natural products in one scheme. Fewer than 13 steps are required for the total synthesis of the compounds, and the total yield typically exceeded 10%.

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  1. Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-Ku, Chiba, 260-8675, Japan

    Hayato Ishikawa

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    Hayato Ishikawa

  2. Chiba University, Chiba, Japan

    Hiromitsu Takayama

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Ishikawa, H. (2023). Collective Synthesis of Monoterpenoid Indole Alkaloids Using Bioinspired Strategies. In: Ishikawa, H., Takayama, H. (eds) New Tide of Natural Product Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-99-1714-3_10

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