Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Versatile Construction of 6-Substituted cis-2,8-Dioxabicyclo[3.3.0]octan-3-ones: Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C

Versatile Construction of 6-Substituted cis-2,8-Dioxabicyclo[3.3.0]octan-3-ones: Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C
Yuriy Slutskyy, Peng Zhao, Young Ho Rhee, Christopher R. Jamison, Larry E. Overman, Juyeol Lee
A short enantioselective synthesis of 6-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-ones is described. The pivotal step is coupling of a tertiary radical generated directly from a tertiary alcohol with a 3-chloro-5-alkoxybutenolide. This strategy is applied toward scalable 14–15 step syntheses of three rearranged spongian diterpenoids: cheloviolenes A and B and dendrillolide C.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04265

DOI: 10.1021/jacs.7b04265

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