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Paper | Special issue | Vol 47, No. 1, 1998, pp.481-490
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)83
Alternative Access to 20-Hydroxyecdysteroid Side Chain by Means of Samarium Iodide-promoted Radical Addition of Tetrahydrofuran to a 20-Keto Steroid

Toshio Honda* and Miho Katoh

*Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Samarium iodide-promoted radical addition of tetrahydrofuran to the 20-keto steroid afforded the adducts as a mixture of diastereomers at the 22-position in high yield. Both adducts were further converted into (20R,22R)-5α-cholestane-3β,20,22,25-tetraol.