STEREOSELECTIVE SYNTHESIS AND THERMAL REARRANGEMENT OF THE 1ST ANALOG OF (7Z)-VITAMIN-D

被引：23

作者：

MAESTRO, MA

SARDINA, FJ

CASTEDO, L

MOURINO, A

机构：

[1] UNIV SANTIAGO DE COMPOSTELA, DEPT QUIM ORGAN, E-15706 SANTIAGO, SPAIN

[2] UNIV SANTIAGO DE COMPOSTELA, CSIC, SECC ALALOIDES, E-15706 SANTIAGO, SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 11期

关键词：

D O I：

10.1021/jo00011a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first (7Z)-vitamin D analogue, 15, was synthesized stereoselectively using, as the key step, Wittig-Horner coupling between an allylphosphine oxide anion and a alpha-benzoyloxy ketone. Compound 15 has the same triene system as the putative 7Z intermediate of the mechanism postulated by Okamura and co-workers for thermally induced [1,5]-sigmatropic hydrogen shifts in vinylallenes. Okamura's hypothesis is supported by the identity of the products of thermally induced [1,7]-sigmatropic hydrogen shifts in 15.

引用

页码：3582 / 3587

页数：6

共 46 条

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