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.

Authors :: Slutskyy Y
Jamison CR
Zhao P
Lee J
Rhee YH
Overman LE
Source :: Journal of the American Chemical Society [J Am Chem Soc] 2017 May 31; Vol. 139 (21), pp. 7192-7195. Date of Electronic Publication: 2017 May 22.
Publication Year :: 2017
Abstract: 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.

Subjects :: Bridged Bicyclo Compounds chemistry
Diterpenes chemistry
Molecular Structure
Stereoisomerism
Bridged Bicyclo Compounds chemical synthesis
Diterpenes chemical synthesis

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