TOTAL SYNTHESIS OF (+/-)-ALPHA-ALLOKAINIC ACID VIA 2 ALLYLSILANE N-ACYLIMINIUM ION REACTIONS

被引：31

作者：

MOOIWEER, HH ^{[1
]}

HIEMSTRA, H ^{[1
]}

SPECKAMP, WN ^{[1
]}

机构：

[1] UNIV AMSTERDAM,DEPT ORGAN CHEM,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS

来源：

TETRAHEDRON | 1991年 / 47卷 / 20-21期

关键词：

D O I：

10.1016/S0040-4020(01)86407-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of racemic alpha-allokainic acid is described, which starts from allylsilane 8 and methoxy- or chloroglycine derivative 9, and proceeds fully stereoselectively in nine steps and 1.1% overall yield. Key steps are the intermolecular N-acyliminium ion coupling of 8 with 9 and an intramolecular allylsilane N-acyliminium ion reaction of 4, which closes the pyrrolidine ring by C4-C5 bond formation. Remarkably, the intramolecular variant of the coupling of 8 with 9 in order to prepare delta-lactone 5 failed to proceed.

引用

页码：3451 / 3462

页数：12

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