Stereoselective reactions. 15. 1 total synthesis of (+)-ivalin by utilizing asymmetric double alkylation reaction of α, β-unsaturated aldimine

K Tomioka, F Masumi, T Yamashita, K Koga

Index: Tomioka; Masumi; Yamashita; Koga Tetrahedron, 1989 , vol. 45, # 3 p. 643 - 650

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Citation Number: 18

Abstract

An asymmetric total synthesis of (+)-ivalin (4), a representative of antileukemic eudesmane sesquiterpenes, is described. The ene-aldehyde (6) was converted to the nearly optically pure alcohol (20) through the asymmetric double a1ky1ation reaction of the chiral ene- enamine (14). The ene-carbonyl cyclization of (25) with tin (IV) chloride afforded the core skeleton (26). The stereoinversion of hydroxyl group and further transformation furnished ( ...