Synthesis of eupomatilone-6 and assignment of its absolute configuration

Gurjar, Mukund K. ; Karumudi, Bhargava ; Ramana, C. V. (2005) Synthesis of eupomatilone-6 and assignment of its absolute configuration Journal of Organic Chemistry, 70 (23). pp. 9658-9661. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0516234

Related URL: http://dx.doi.org/10.1021/jo0516234

Abstract

The Zn-mediated Barbier reaction of the biarylaldehyde 8 with crotyl bromide followed by hydroboration and oxidation provided the γ-butyrolactones 4 and 5. The stereoselective installation of methyl group at C-3 by using LiHMDS and MeI completed the synthesis of racemic eupomatilone-6 (2) and its diastereomer 3. The spectroscopic data of 2 was in full agreement with reported spectra of natural product, thus confirming the revised relative configuration of eupomatilone-6. Similarly, an optically active (3R,4R,5S)-isomer of eupomatilone-6 (23) was prepared in which the aldol reaction with thiazolidinethione as a chiral auxiliary was employed as a key step. On the basis of the spectroscopic data and optical rotation values of 23, the absolute configuration of eupomatilone-6 was proposed.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:11359
Deposited On:09 Nov 2010 05:04
Last Modified:02 Jun 2011 09:42

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