A SYNTHETIC APPROACH TO THE SQUALESTATINS AND ZARAGOZIC ACIDS - INTRODUCTION OF THE C5 STEREOCENTER VIA AN ESTER ENOLATE CLAISEN REARRANGEMENT - THE X-RAY CRYSTAL-STRUCTURE OF AN INTERMEDIATE

被引：22

作者：

GABLE, RW ^{[1
]}

MCVINISH, LM ^{[1
]}

RIZZACASA, MA ^{[1
]}

机构：

[1] UNIV MELBOURNE,SCH CHEM,PARKVILLE,VIC 3052,AUSTRALIA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1994年 / 47卷 / 08期

关键词：

D O I：

10.1071/CH9941537

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In an overall plan to synthesize the anti-cholesterol agents the squalestatins and zaragozic acids, introduction of the C 5 stereochemistry was achieved via an Ireland-Claisen rearrangement of the allyl ester (7) followed by methylation, which gives the esters (8) and (9) in a ratio of 5.7:1. The structure of the alcohol (11) derived from the minor isomer (9) was confirmed by X-ray crystallography.

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页码：1537 / 1544

页数：8

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