Highly stereoselective 1,4-addition of the enolate generated from 6-deoxy-D-glucopyranoside-derived propionyl ester to methyl crotonate: Application to total synthesis of (-)-lasiol

摘要

1,4-Addition of the enolate generated from methyl 6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-4-O-propionyl-alpha-D-gluco- pyranoside to methyl crotonate provided a single anti-adduct with exceptionally high stereoselectivity. From this adduct, (-)-lasiol, an acyclic monoterpene alcohol isolated from the males of Lasius meridionalis ants, was synthesized concisely. [References: 17]