Stereoselective total synthesis of stagonolide-C

The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamag...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 23; no. 15-16; pp. 1186 - 1197
Main Authors Venkatesham, Akkaladevi, Nagaiah, Kommu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 31.08.2012
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ALCOHOLS
STAGONOSPORA-CIRSII
ALDOL ADDITIONS
PHYTOTOXIC NONENOLIDE
POTENTIAL MYCOHERBICIDE
STEREOCHEMISTRY
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Summary:The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2012.07.015