Rection of Enohexopyranoside Acetates with Lithium Dimethylcuprate(I) and Its Application to Synthesis of Prelog-Djerassi Lactone

Article abstract of DOI:10.1246/bcsj.60.1441

In the reaction of two 2-O-acetyl-3-enohexopyranosides and four 4-O-acetyl-2-enohexopyranosides including 2-C-methyl and 4-C methyl derivatives, respectively, with lithium dimethylcuprate(I), anti S_N2' substitution was proved to be preferential, giving the corresponding C-methylated derivatives.On the other hand, S_N2 substitution occurred in the reaction of the 2-enopyranoside without methyl branch and D-glucal triacetate