Stereoselective Functionalization of Dihydropyran‐3‐ols: Application to the Synthesis of Enantiopure Ethyl Deoxymonate B | Zendy

Fernández de la Pradilla Roberto | Zendy; Lwoff Nadia | Zendy; Viso Alma | Zendy

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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)

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