Regioselective 1,6-conjugate addition of organocuprate reagents to γ-alkylidenebutenolides

Abstract

This work describes the study of behavior of the d-substituted and d-non-substituted exo-cyclic double bond of c-alkylidenebutenolides with dialkylcuprates. The addition reaction was found to be regioselective to afford the 1,6-conjugate adduct up to 87% yield.

Gilman reagent toward the synthesis of natural products

“…2). 16,17 Gilman reagent has been extensively employed in the synthesis of a number of architecturally unique natural products, such as the C1 to C9 framework of callipeltoside-a 3 (isolated from a marine sponge Callipelta sp), which is an anti-HIV agent, liconadin A 4 (a Lycopodium alkaloid) (Fig. 3) 18,19 and furosesquiterpenes i.e., isopallescensin-A 5, isopallescensin-1 6, 5-desmethyl-4,5-dehydromicrocionin-1 7, which are best known for their diverse biological activities (Fig.…”