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Biogenetically inspired synthesis and skeletal diversification of indole alkaloids

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Title: Biogenetically inspired synthesis and skeletal diversification of indole alkaloids
Authors: Mizoguchi, Haruki Browse this author
Oikawa, Hideaki Browse this author →KAKEN DB
Oguri, Hiroki Browse this author →KAKEN DB
Issue Date: Jan-2014
Publisher: Nature publishing group
Journal Title: Nature chemistry
Volume: 6
Issue: 1
Start Page: 57
End Page: 64
Publisher DOI: 10.1038/NCHEM.1798
PMID: 24345948
Abstract: To access architecturally complex natural products, chemists usually devise a customized synthetic strategy for constructing a single target skeleton. In contrast, biosynthetic assembly lines often employ divergent intramolecular cyclizations of a polyunsaturated common intermediate to produce diverse arrays of scaffolds. With the aim of integrating such biogenetic strategies, we show the development of an artificial divergent assembly line generating unprecedented numbers of scaffold variations of terpenoid indole alkaloids. This approach not only allows practical access to multipotent intermediates, but also enables systematic diversification of skeletal, stereochemical and functional group properties without structural simplification of naturally occurring alkaloids. Three distinct modes of [412] cyclizations and two types of redox-mediated annulations provided divergent access to five skeletally distinct scaffolds involving iboga-, aspidosperma-, andranginine- and ngouniensine-type skeletons and a non-natural variant within six to nine steps from tryptamine. The efficiency of our approach was demonstrated by successful total syntheses of (+/-)-vincadifformine, (+/-)-andranginine and (2)-catharanthine.
Type: article (author version)
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 大栗 博毅

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