Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: A novel protocol for the stereoselective synthesis of C-1-C-8 and C-15-C-21 Subunits of (+)-discodermolide

Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective alpha-deoxygenation provides 1,3-trans-beta-hydroxy-delta-lactones stereoselectively. This protocol has been applied for the synthesis of C-1-C-8 and C-15-C-21 subunits of (+)-discodermolide.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 69; no. 19; pp. 6294 - 6304
Main Authors Ramachandran, PV, Prabhudas, B, Chandra, JS, Reddy, MVR
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 17.09.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MEDIATED ALDOL REACTIONS
STABILIZING AGENT DISCODERMOLIDE
ASYMMETRIC-SYNTHESIS
PRACTICAL SYNTHESIS
CHIRAL SYNTHESIS
LARGE-SCALE SYNTHESIS
OLEFIN METATHESIS
STEREOGENIC CENTERS
NATURAL-PRODUCT (+)-DISCODERMOLIDE
FRAGMENTS C1-6
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Summary:Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective alpha-deoxygenation provides 1,3-trans-beta-hydroxy-delta-lactones stereoselectively. This protocol has been applied for the synthesis of C-1-C-8 and C-15-C-21 subunits of (+)-discodermolide.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0492416