SYNTHETIC STUDIES ON CALYCULIN-A - A CONVENIENT ASYMMETRIC-SYNTHESIS OF ANTI-VICINAL DIOLS

被引：21

作者：

BARRETT, AGM ^{[1
]}

MALECHA, JW ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 14期

关键词：

D O I：

10.1039/p19940001901

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

anti-Vicinal diols have been prepared with excellent relative and-absolute stereocontrol via the reaction of aldehydes with B-{3-[(diisopropylamino)dimethylsilyl]allyl}diisopinocampheylborane in THF and diethyl ether and work-up using potassium fluoride. potassium hydrogen carbonate and hydrogen peroxide in aqueous methanol. Absolute stereoselectivities of reactions were determined by conversion of four product diols into bis[(R)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetate] esters. The reactions are relevant to the synthesis of the marine phosphatase inhibitor calyculin A.

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页码：1901 / 1905

页数：5

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