ENANTIOSELECTIVE AND DIASTEREOSELECTIVE TRANSFORMATIONS OF CYCLOHEPTATRIENE TO SUGARS AND RELATED PRODUCTS

Authors
JOHNSON CR GOLEBIOWSKI A STEENSMA DH SCIALDONE MA
Citation
Cr. Johnson et al., ENANTIOSELECTIVE AND DIASTEREOSELECTIVE TRANSFORMATIONS OF CYCLOHEPTATRIENE TO SUGARS AND RELATED PRODUCTS, Journal of organic chemistry, 58(25), 1993, pp. 7185-7194
Citations number
57
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
25
Year of publication
1993
Pages
7185 - 7194
Database
ISI
SICI code
0022-3263(1993)58:25<7185:EADTOC>2.0.ZU;2-F
Abstract
Both meso diastereomers of t-butyldimethylsilyl)oxy]-2-cycloheptene-1, 4-diol, prepared from cycloheptatriene, have been enzymatically asymme trized by conversion to monoacetates using Pseudomonas cepacia lipase in isopropenyl acetate. A study of protecting group manipulations, dia stereoselective oxidations, and regioselective ring openings utilizing these enantiopure monacetates which results in the synthesis of all p ossible methyl 2,4-dideoxyhexopyranosides is described.