Asymmetric syntheses of epohelmins A and B by In-mediated allylation.
A diastereoselective new approach for the synthesis of trans-4-hydroxy-5-allyl-2-pyrrolidinone 9 has been developed through In-mediated allylation of α-chiral aldimine 8 with allyl bromide. The stereochemistry at the C-2 stereogenic center of 9 was controlled by both the α-OTBS substitution and the sulfinamide moiety. The utility of this asymmetric allylation is demonstrated by the asymmetric syntheses of epohelmins A (4) and B (10).
Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China. sicm@fudan.edu.cn bgwei1974@fudan.edu.cn.
Yi-Wen
YW
Liu
Pan
P
Han
Wen
W
Zhou
Zhuo-Ya
ZY
Mao
Chang-Mei
CM
Si
Bang-Guo
BG
Wei
D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis / Q000737:chemistry
D000498:Allyl Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011760:Pyrrolidinones; D013452:Sulfonium Compounds; C494514:epohelmin A; C494515:epohelmin B; C050431:allyl bromide; C028537:2-pyrrolidone