Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease

Yadav, J. S. ; Deshpande, P. K. ; Sharma, G. V. M. (1992) Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease Tetrahedron, 48 (21). pp. 4465-4474. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)80454-3

Abstract

A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd°-CuI catalysed coupling of (S )-halovinylalcohol with acetylenic moiety is described. The required optically pure chlorovinylalcohols or bromovinylalcohols have been prepared from epoxy chlorides, obtained by Sharpless asymmetric epoxidation of allylic alcohols.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Coriolic Acid; 15,16-didehydrocoriolic Acid; Chlorovinylalcohols; Bromovinylalcohols; Chiral Alkynols
ID Code:58746
Deposited On:02 Sep 2011 03:08
Last Modified:02 Sep 2011 03:08

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