SYNTHESIS OF POLYPROPIONATE SUBUNITS BY SN2' ADDITION OF CUPRATES TO NONRACEMIC ACYCLIC VINYLOXIRANES

被引：34

作者：

MARSHALL, JA

BLOUGH, BE

机构：

[1] Department of Chemistry University of South Carolina, Columbia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 05期

关键词：

D O I：

10.1021/jo00292a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic sequences have been devised for conversion of the chiral pool ester 1 to differentially protected polypropionate subunit polyols 11, 13, 18, and 20. The following stereochemically significant steps were employed: (1) reagent directed Sharpless epoxidation of allylic alcohol 4 (75:25); (2) substrate directed anti SN2’ addition of MeCu(CN)Li to vinyloxirane 8 (>95:5); (3) substrate directed homogeneous hydrogenation of homoallylic alcohol 10 (94:6); (4) substrate directed hydroboration of allylic alcohol 14 (88:12). The stereochemistry of alcohol 13 was confirmed through conversion to lactone 27 an intermediate in Suzuki's synthesis of protomycinolide. © 1990, American Chemical Society. All rights reserved.

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页码：1540 / 1547

页数：8

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