Concise formal synthesis of (-)-7-deoxyloganin via n-heterocyclic carbene catalysed rearrangement of alpha,beta-unsaturated enol esters

Lisa Candish, David Lupton

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Abstract

NHC catalysed rearrangement of alpha,beta-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated alpha,beta-unsaturated acids provides the cyclopentapyranone core of (-)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps starting from (-)-citronellal. The elaboration to the natural product has been investigated using two new approaches. The most successful intercepts our previous work on (-)-7-deoxyloganin (1) allowing completion of a formal total synthesis in 10-steps.
Original languageEnglish
Pages (from-to)8182 - 8189
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number23
DOIs
Publication statusPublished - 2011

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