CONTROLLING BENZYLIC FUNCTIONALITY AND STEREOCHEMISTRY .2. SYNTHESIS OF THE PSEUDOPTEROSIN AGLYCONE

被引：35

作者：

MCCOMBIE, SW

COX, B

GANGULY, AK

机构：

[1] Chemical Research, Schering-Plough Corporation, Bloomfield, NJ 07003

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)71243-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homologation, cyclisation, and reduction converted the tetralin (2) to the hexahydrophenalenol (8), which was methylated to afford (19) via alkoxide-directed metalation. The degree of stereoselectivity resulting from reactions of (19) and congeners with allylsilane - Lewis acid combinations was markedly dependent upon substitution patterns, whereas Et2AlCN-SnCl4 produced pseudoaxial nitriles. The trimethyl nitrile (24) was elaborated to the pseudopterosin aglycone (4).

引用

页码：2087 / 2090

页数：4

共 19 条

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