TRANSFORMATIONS OF HYDROXY CYCLIC SULFATES - STEREOSPECIFIC CONVERSION INTO 2,3,5-TRISUBSTITUTED TETRAHYDROFURANS

被引：16

作者：

KALANTAR, TH ^{[1
]}

SHARPLESS, KB ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

ACTA CHEMICA SCANDINAVICA | 1993年 / 47卷 / 03期

关键词：

D O I：

10.3891/acta.chem.scand.47-0307

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

1,2-Cyclic sulfates have been prepared from 0-protected ricinoleate and ricinelaidate esters. Upon deprotection of the 12-hydroxy moiety, the resulting 12-hydroxy-9,10-cyclic sulfates underwent stereospecific cyclization to the corresponding 2,3,5-trisubstituted tetrahydrofurans. The cyclization occurs by backside attack of the hydroxy oxygen on the distal carbon of the 1,2-cyclic sulfate, with inversion at that center.

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页码：307 / 313

页数：7

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