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Asymmetric Total Synthesis of Brasilicardins

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Title: Asymmetric Total Synthesis of Brasilicardins
Authors: Yoshimura, Fumihiko Browse this author →KAKEN DB
Itoh, Ryusei Browse this author
Torizuka, Makoto Browse this author
Mori, Genki Browse this author
Tanino, Keiji Browse this author →KAKEN DB
Keywords: brasilicardins
Michael addition
natural products
quaternary stereocenters
total synthesis
Issue Date: 21-Dec-2018
Publisher: Wiley
Journal Title: Angewandte Chemie International Edition
Volume: 57
Issue: 52
Start Page: 17161
End Page: 17167
Publisher DOI: 10.1002/anie.201811403
Abstract: Brasilicardins, bacterial diterpenoid natural products that display highly potent immunosuppressive activity, are promising immunosuppressant drug candidates. Structurally, they can be described as hybrids of terpenoids, amino acids, and saccharides, and share a characteristic highly strained anti‐syn‐anti‐fused perhydrophenanthrene terpenoid scaffold (ABC‐ring system) with two quaternary asymmetric carbon atoms. A unified and stereoselective total synthesis of all four brasilicardins has been designed based on the strategic use of an intramolecular conjugate addition. The ABC‐ring system was initially constructed with high stereocontrol by novel intramolecular conjugate additions of Weinreb amides and in situ generated (Z)‐vinyl copper species. The late‐stage common intermediate was subjected to stereoselective installation of the amino acid component, followed by introduction of the saccharide unit via glycosylation to accomplish the total synthesis of brasilicardins A–D. Our synthesis offers opportunities to synthesize various brasilicardin analogues for biological and pharmacological investigations.
Rights: This is the peer reviewed version of the following article:Angewandte Chemie (International ed.) 57(52) December 21 2018, pp.17161-17167 which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
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: 吉村 文彦

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