title: Stereocontrolled synthesis of the AB rings of samaderine C.
abstract: 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.
authors.affiliation: Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
authors.forename: David J
authors.initials: DJ
authors.lastname: Burns
authors.forename: Stefan
authors.initials: S
authors.lastname: Mommer
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
authors.forename: Adrian C
authors.initials: AC
authors.lastname: Whitwood
authors.forename: Shuji
authors.initials: S
authors.lastname: Hachisu
mesh_terms: D006900:Hydroxylation; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D036702:Quassins / Q000138:chemical synthesis* / Q000737:chemistry; D029641:Simaroubaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D036702:Quassins; C432980:samaderin C