The total synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalyzed rearrangement of alpha,beta-unsaturated enol esters

Lisa Candish, David W Lupton

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Abstract

The diastereoselective N-heterocyclic carbene (NHC) catalyzed rearrangement of alpha,beta-unsaturated enol ester (S)-2b has been used to assemble dihydropyranone (S)-3b, a material embodying the bicyclic core of the iridoid family of natural products. Elaboration of this intermediate, by chemoselective reduction followed by stereoselective beta-glycosylation, has allowed the total synthesis of (-)-7-deoxyloganin (1) to be achieved in four subsequent steps.
Original languageEnglish
Pages (from-to)4836 - 4839
Number of pages4
JournalOrganic Letters
Volume12
Issue number21
DOIs
Publication statusPublished - 2010

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