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

Marie-Gabrielle Braun (1) , Aurélie Vincent (1) , Medhi Boumediene (1) , Joëlle Prunet (2)

1 DCSO - Laboratoire de synthèse organique
2 WestCHEM

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. © 2011 American Chemical Society.

Domains: Chemical Sciences; Organic chemistry

Marie-Gabrielle Braun, Aurélie Vincent, Medhi Boumediene, Joëlle Prunet. Highly demanding cross-metathesis in the synthesis of the C16-C30 fragment of dolabelide C. Journal of Organic Chemistry, 2011, 76 (12), pp.4921-4929. ⟨10.1021/jo200466t⟩. ⟨hal-00951226⟩