Enantioselective total synthesis of cis-trikentrin B

被引：43

作者：

Lee, M ^{[1
]}

Ikeda, I ^{[1
]}

Kawabe, T ^{[1
]}

Mori, S ^{[1
]}

Kanematsu, K ^{[1
]}

机构：

[1] KYUSHU UNIV 62,FAC PHARMACEUT SCI,INST SYNTHET ORGAN CHEM,HIGASHI KU,FUKUOKA 81282,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 10期

关键词：

D O I：

10.1021/jo951767q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.

引用

页码：3406 / 3416

页数：11

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