EFFICIENT TOTAL SYNTHESIS OF AI-77-B, A GASTROPROTECTIVE SUBSTANCE FROM BACILLUS-PUMILUS AI-77

被引：98

作者：

HAMADA, Y

HARA, O

KAWAI, A

KOHNO, Y

SHIOIRI, T

机构：

[1] Faculty of Pharmaceutical Sciences, Nagoya City University Tanabe-dori, Mizuho-ku, Nagoya

来源：

TETRAHEDRON | 1991年 / 47卷 / 40期

关键词：

AI-77-B; DIHYDROISOCOUMARIN; HYDROXY AMINO ACID; STEREOSELECTIVE OSMYLATION; INTRAMOLECULAR PINNER REACTION;

D O I：

10.1016/S0040-4020(01)82406-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

First total synthesis of AI-77-B (1), a gastroprotective substance from Bacillus pumilus AI-77, was achieved in a stereoselective and convergent manner. In this synthesis, the dihydroisocoumarin part 2 was constructed in one step through 1,2-addition of the benzylic anion 17b to Boc-L-leucinal 7b. The hydroxy amino acid 4 was elaborated from (R)-glutamic acid in a highly stereoselective manner. Condensation of 2.HCl and 4, intramolecular Pinner reaction, followed by mild hydrolysis afforded AI-77-B (1).

引用

收藏

页码：8635 / 8652

页数：18

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