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- Title
Enantioselective Total Synthesis of Macfarlandin C, a Spongian Diterpenoid Harboring a Concave‐Substituted cis‐Dioxabicyclo[3.3.0]octanone Fragment.
- Authors
Allred, Tyler K.; Dieskau, André P.; Zhao, Peng; Lackner, Gregory L.; Overman, Larry E.
- Abstract
The enantioselective total synthesis of the rearranged spongian diterpenoid (−)‐macfarlandin C is reported. This is the first synthesis of a rearranged spongian diterpenoid in which the bulky hydrocarbon fragment is joined via a quaternary carbon to the highly hindered concave face of the cis‐2,8‐dioxabicyclo[3.3.0]octan‐3‐one moiety. The strategy involves a late‐stage fragment coupling between a tertiary carbon radical and an electrophilic butenolide resulting in the stereoselective formation of vicinal quaternary and tertiary stereocenters. A stereoselective Mukaiyama hydration that orients a pendant carboxymethyl side chain cis to the bulky octahydronapthalene substituent was pivotal in fashioning the challenging concave‐substituted cis‐dioxabicyclo[3.3.0]octanone fragment.
- Subjects
HYDRATION; CYCLOPENTANE; CARBON; HYDROCARBONS
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 15, p6327
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201916753