FACILE PREPARATION OF (+/-)-12-EPIPROSTAGLANDINS FROM 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-ONE VIA AN ALL-CIS-FORMYLLACTONE RELATED TO COREY LACTONE

被引：56

作者：

VIONNET, JP ^{[1
]}

RENAUD, P ^{[1
]}

机构：

[1] UNIV FRIBOURG,INST CHIM ORGAN,CH-1700 FRIBOURG,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1994年 / 77卷 / 07期

关键词：

D O I：

10.1002/hlca.19940770710

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The bicyclic monoselenoacetal 7, easily obtained from (+/-)-7-oxabicyclo[2.2.1]hept-5-en-2-one (6) via a radical addition-acyl migration sequence, was converted to racemic 12-epiprostaglandins 3 and 4. The key intermediate was the all-cis-formyllactone 2b related to Corey lactone (see 12; Scheme 1). The presence of a (tert-butyl)-dimethylsilyl protective group for the 11-OH substituent (prostaglandin numbering) was found to be crucial in avoiding beta-elimination and epimerization during the Wittig-Horner reaction (Scheme 2). Epimerization at C(12) at the formyllactone stage (see 2b) was also possible and gave the known precursor 1b of naturally occurring prostaglandins and analogs.

引用

页码：1781 / 1790

页数：10

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