Stereocontrolled synthesis of the AB rings of samaderine C

TY - JOUR

T1 - Stereocontrolled synthesis of the AB rings of samaderine C

AU - Burns, David J

AU - Mommer, Stefan

AU - O'Brien, Peter

AU - Taylor, Richard J K

AU - Whitwood, Adrian C

AU - Hachisu, Shuji

PY - 2013/1/18

Y1 - 2013/1/18

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84872550250&partnerID=8YFLogxK

U2 - 10.1021/ol303385a

DO - 10.1021/ol303385a

M3 - Article

C2 - 23302065

SN - 1523-7060

VL - 15

SP - 394

EP - 397

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -