Highly demanding cross metathesis in the synthesis of the C16-C30 fragment of dolabelide C

Braun, M.G., Vincent, A., Boumediene, M. and Prunet, J. (2011) Highly demanding cross metathesis in the synthesis of the C16-C30 fragment of dolabelide C. Journal of Organic Chemistry, 76(12), pp. 4921-4929. (doi:10.1021/jo200466t)

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Publisher's URL: http://dx.doi.org/10.1021/jo200466t

Abstract

A highly demanding cross-metathesis (CM) reaction for the formation of the C24–C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16–C30 fragment of dolabelide C is reported.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Prunet, Dr Joelle
Authors: Braun, M.G., Vincent, A., Boumediene, M., and Prunet, J.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Journal Abbr.:J. Org. Chem.
ISSN:0022-3263
ISSN (Online):1520-6904
Published Online:02 May 2011
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