Development of Stereodivergent Synthesis of Skipped Dienes and Application to Unified Total Synthesis of Madangamine Alkaloids

被引：0

作者：

Sato, Takaaki ^{[1
]}

机构：

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

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2022年 / 80卷 / 04期

基金：

爱尔兰科学基金会;

关键词：

allene; hydroboration; madangamine; skipped diene; total synthesis; PD-CATALYZED CYCLOISOMERIZATION; 1ST ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIAZATRICYCLIC CORE; GLIDING BACTERIA; STEREOSPECIFIC SYNTHESIS; SUBSTITUTED 1,4-DIENES; ASYMMETRIC-SYNTHESIS; ALLYLIC CARBONATES; UNSATURATED ESTERS;

D O I：

10.5059/yukigoseikyokaishi.80.343

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A skipped diene (1,4-diene)is an important structural motif found in a variety of biologically active natural products. We report the stereodivergent method, consisting of hydroboration of allenes and the Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration of allenes is especially useful because both Eallylic and Z-allylic alcohols are obtained by simply changing the organoborane reagent. While use of 9-BBN provides E-allylic alcohols as thermodynamic products, the reaction with HB(Sia)(2) gives Z-allylic alcohols as kinetic products. The developed method was successfully applied to the unified total synthesis of madangamine alkaloids.

引用

页码：343 / 356

页数：14

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