Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

Seiya Katahara; Yasukazu Sugiyama; Mina Yamane; Yukinori Komiya; Takaaki Sato; Noritaka Chida

doi:10.1021/acs.orglett.1c00735

Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

Seiya Katahara, Yasukazu Sugiyama, Mina Yamane, Yukinori Komiya, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

A five-step total synthesis of (±)-aspidospermidine (1) based on a lactam strategy is reported. Our synthesis features an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade to give a tricyclic ketone intermediate from a simple lactam via an azomethine ylide. The developed strategy enables easily available lactams to be used as stable surrogates of multisubstituted amines and would be applicable to a unified total synthesis of complex Aspidosperma alkaloids.

Original language	English
Pages (from-to)	3058-3063
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.1c00735
Publication status	Published - 2021 Apr 16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c00735

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abstract = "A five-step total synthesis of (±)-aspidospermidine (1) based on a lactam strategy is reported. Our synthesis features an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade to give a tricyclic ketone intermediate from a simple lactam via an azomethine ylide. The developed strategy enables easily available lactams to be used as stable surrogates of multisubstituted amines and would be applicable to a unified total synthesis of complex Aspidosperma alkaloids. ",

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T1 - Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

AU - Katahara, Seiya

AU - Sugiyama, Yasukazu

AU - Yamane, Mina

AU - Komiya, Yukinori

AU - Sato, Takaaki

AU - Chida, Noritaka

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (C) from MEXT (18K05127) and a JSPS fellowship to S.K. (19J10048). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/4/16

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AB - A five-step total synthesis of (±)-aspidospermidine (1) based on a lactam strategy is reported. Our synthesis features an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade to give a tricyclic ketone intermediate from a simple lactam via an azomethine ylide. The developed strategy enables easily available lactams to be used as stable surrogates of multisubstituted amines and would be applicable to a unified total synthesis of complex Aspidosperma alkaloids.

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Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

Abstract

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