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Stereoselective Functionalization of Dihydropyran‐3‐ols: Application to the Synthesis of Enantiopure Ethyl Deoxymonate B
Author(s) -
Fernández de la Pradilla Roberto,
Lwoff Nadia,
Viso Alma
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801133
Subject(s) - dihydropyran , enantiopure drug , chemistry , stereoselectivity , dihydroxylation , organic chemistry , stereochemistry , enantioselective synthesis , catalysis
The behavior of readily available enantiopure cis and trans 3,6‐disubstituted dihydropyran‐3‐ols and derivatives in epoxidation, osmium‐catalyzed dihydroxylations, S N 2′, and Claisen‐related processes has been examined. The highly diastereoselective dihydroxylation of a suitably functionalized cis 3,6‐disubstituted dihydropyran‐3‐ol has been used in the synthesis of ethyl deoxymonate B from a 3‐sulfinyldihydropyran intermediate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)