Stereocontrolled synthesis of the AB rings of samaderine C

David J Burns, Stefan Mommer, Peter O'Brien, Richard J K Taylor, Adrian C Whitwood, Shuji Hachisu

Research output: Contribution to journalArticlepeer-review


A concise synthesis of the AB rings of samaderine C (12 steps, 8 isolation steps, 7.8% overall yield), a quassinoid with antifeedant and insecticidal activity, is described. The development of the first general approach to the trans-1,2-diol A-ring motif in samaderine C and other quassinoids is a key feature. The trans-1,2-diol is crafted via stereoselective α-hydroxylation (of a silyl enol ether) and reduction, a strategy that has much potential for quassinoid synthesis.
Original languageEnglish
Pages (from-to)394-7
Number of pages4
JournalOrganic Letters
Issue number2
Early online date9 Jan 2013
Publication statusPublished - 18 Jan 2013

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