Unified Total Synthesis of Madangamine Alkaloids

被引：12

作者：

Suto, Takahiro ^{[1
]}

Yanagita, Yuta ^{[1
]}

Nagashima, Yoshiyuki ^{[1
]}

Takikawa, Shinsaku ^{[1
]}

Kurosu, Yasuhiro ^{[1
]}

Matsuo, Naoya ^{[1
]}

Miura, Kazuki ^{[1
]}

Simizu, Siro ^{[1
]}

Sato, Takaaki ^{[1
]}

Chida, Noritaka ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2019年 / 92卷 / 03期

关键词：

Madangamine; Skipped diene; Total synthesis; PD-CATALYZED CYCLOISOMERIZATION; 1ST ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIAZATRICYCLIC CORE; SKIPPED DIENES; STEREOSPECIFIC SYNTHESIS; SUBSTITUTED 1,4-DIENES; ALLYLIC CARBONATES; UNSATURATED ESTERS; MARINE ALKALOIDS;

D O I：

10.1246/bcsj.20180334

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 A-E. The synthetic madangamine alkaloids exhibited inhibitory activities against a variety of human cancer cell lines.

引用

页码：545 / 571

页数：27

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