Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 15, Pages 6268-6272Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201916753
Keywords
C-C coupling; natural product synthesis; photoredox chemistry; radical chemistry; terpene synthesis
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Funding
- National Science Foundation [CHE-1265964, CHE-1661612]
- National Institute of General Medical Sciences [R01-GM098601]
- ACS Organic Chemistry Division
- German Academic Exchange Service (DAAD)
- NIH
- NSF
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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.
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