ENANTIOSELECTIVE AND DIASTEREOSELECTIVE TRANSFORMATIONS OF CYCLOHEPTATRIENE TO SUGARS AND RELATED PRODUCTS

被引：32

作者：

JOHNSON, CR

GOLEBIOWSKI, A

STEENSMA, DH

SCIALDONE, MA

机构：

[1] Department of Chemistry, Wayne State University, Detroit

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 25期

关键词：

D O I：

10.1021/jo00077a049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both meso diastereomers of 6-[(tert-butyldimethylsilyl)oxy]-2-cycloheptene-1,4-diol, prepared from cycloheptatriene, have been enzymatically asymmetrized by conversion to monoacetates using Pseudomonas cepacia lipase in isopropenyl acetate. A study of protecting group manipulations, diastereoselective oxidations, and regioselective ring openings utilizing these enantiopure monacetates which results in the synthesis of all possible methyl 2,4-dideoxyhexopyranosides is described.

引用

页码：7185 / 7194

页数：10

共 57 条

[1]

BACKVALL JE, 1984, J ORG CHEM, V49, P4619

[2] TIN-DIRECTED BAEYER-VILLIGER AND BECKMANN FRAGMENTATIONS [J].