First total synthesis of the E- and Z-isomers of cytospolide-D

A simple, convergent, and efficient approach for the total synthesis of the bioactive E- and Z-isomers of cytospolide-D is described. The key features of the synthetic strategy include stereoselective methylation, regioselective epoxide opening, olefin cross-metathesis, and a Yamaguchi protocol reac...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2014-01, Vol.25 (2), p.148-155
Main Authors: Kamal, Ahmed, Balakrishna, Moku, Reddy, Papagari Venkat, Rahim, Abdul
Format: Article
Language:English
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Summary:A simple, convergent, and efficient approach for the total synthesis of the bioactive E- and Z-isomers of cytospolide-D is described. The key features of the synthetic strategy include stereoselective methylation, regioselective epoxide opening, olefin cross-metathesis, and a Yamaguchi protocol reaction for the formation of the E-olefinic geometry of the 10 membered ring; Steglich esterification and ring-closing metathesis reaction for the formation of the 10 membered ring with a Z-olefinic geometry in the skeleton. l-Malic acid was used as a chiral pool starting material for the construction of the olefinic acid fragment while d-mannitol was used as a chiral pool starting material for the building of the olefinic alcohol fragment.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2013.12.004