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Paper | Regular issue | Vol 34, No. 12, 1992, pp.2323-2330
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6131
Stereoselective Total Synthesis of (±)-Peperomin C

Raymundo Cruz-Almanza* and Fernando Padilla Higareda

*Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior Ciudad Universitaria, Coyoacán, 04510, México, D.F., México

Abstract

A simple and efficient stereoselective total synthesis of (±)-peperomin C(1) was performed employing the 1,4-addition reaction of the organolithium salt (10) to the 3-methyl-2(5H)-furanone (7) catalized by cuprous iodide as the key steps. On the other hand, α-methyl-β-(diphenylmethyl)-γ-butyrolactone (4), an analogous of peperomin C, was also synthetized by the 1,4-addition reaction of the organocuprate (6) on the same 3-methyl-2(5H)furanone (7).