Progress towards the asymmetric total synthesis of Eupomatilone 5

ORGN 720

Soumya Mitra, smitra@chemistry.ohio-state.edu, Department of Chemistry, The Ohio State University, 100 W 18th Avenue, Newman Wolfrom Laboratory of Chemistry, Columbus, OH 43210-1185 and Robert S. Coleman, coleman@chemistry.ohio-state.edu, Department of Chemistry, Ohio State University, 100 West 18th Ave., Columbus, OH 43210.
Eupomatilones are structurally novel lignans isolated from Eupomatia bennettii containing an alpha-methylene gamma-lactone moeity attached to electron rich biaryl systems. This work reports the development of a strategy towards the total synthesis of Eupomatilone-5 via an asymmetric crotylation reaction. The crotyl fragment was generated by a Baylis-Hillman/allylic rearrangement reaction sequence. The aldehyde precursor was synthesized by a highly efficient Suzuki-Miyaura biaryl cross coupling reaction. Recent progress towards the completion of the synthetic route will be presented. A retrosynthetic scheme for the short asymmetric synthetic strategy is shown below.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006