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

Author:
Garnsey, Michelle R., Slutskyy, Yuriy, Jamison, Christopher R., Zhao, Peng, Lee, Juyeol, Rhee, Young Ho, Overman, Larry E.
Source:
Journal of organic chemistry 2017 v.83 no.13 pp. 6958-6976
ISSN:
1520-6904
Subject:
carbon, chemical reactions, chemical structure, diterpenoids, enantioselectivity, organic chemistry
Abstract:
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.
Agid:
6046639