Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C via Convergent Fragment Coupling Using a Tertiary Carbon Radical

Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C via Convergent Fragment Coupling Using a Tertiary Carbon Radical
Peng Zhao, Yuriy Slutskyy, Larry E. Overman, Juyeol Lee, Michelle R. Garnsey, Young Ho Rhee, Christopher R. Jamison
The development of a convergent fragment coupling strategy for the enantioselective total syntheses of a group of rearranged spongian diterpenoids that harbor the cis-2,8-dioxabicyclo[3.3.0]octan-3-one unit is described. The key bond disconnection relies on a late-stage fragment coupling between a tertiary carbon radical and an electron-deficient alkene to unite two ring systems and form two new stereocenters, one of which is quaternary, in a stereoselective and efficient manner. 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/acs.joc.7b02458

DOI: 10.1021/acs.joc.7b02458

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