Unified Total Synthesis of Madangamine Alkaloids

Takahiro Suto, Yuta Yanagita, Yoshiyuki Nagashima, Shinsaku Takikawa, Yasuhiro Kurosu, Naoya Matsuo, Kazuki Miura, Siro Simizu, Takaaki Sato, Noritaka Chida

研究成果: Article査読

8 被引用数 (Scopus)

抄録

The full details of a unified total synthesis of madangamine alkaloids are disclosed. Our central strategy is based on the construction of a common ABCE-tetracyclic system, followed by the late-stage installation of various D-rings. The common intermediate is assembled through N-acyliminium cyclization of a propargylsilane, and formation of the (Z,Z)-skipped diene. Stereoselective synthesis of the (Z,Z)-skipped diene is especially challenging, and is accomplished by the combination of Z-selective hydroboration of the 1,1-disubstituted allene and subsequent Migita-Kosugi-Stille coupling. Macrocyclic alkylation enables the late-stage variation of the D-rings on the common tetracyclic intermediate, resulting in the collective total syntheses of madangamines AE. The synthetic madangamine alkaloids exhibited inhibitory activities against a variety of human cancer cell lines.

本文言語English
ページ(範囲)545-571
ページ数27
ジャーナルBulletin of the Chemical Society of Japan
92
3
DOI
出版ステータスPublished - 2019

ASJC Scopus subject areas

  • 化学 (全般)

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