A general enantioselective route to the chamigrene natural product family

David E. White, Ian C. Stewart, Brinton A. Seashore-Ludlow, Robert H. Grubbs, Brian M. Stoltz

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and α-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented.
Original languageEnglish (US)
Pages (from-to)4668-4686
Number of pages19
JournalTetrahedron
Volume66
Issue number26
DOIs
StatePublished - Jun 2010
Externally publishedYes

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