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Communication | Regular issue | Vol 20, No. 11, 1983, pp.2159-2162
Published online, 1st January, 1970
DOI: 10.3987/R-1983-11-2159
A New Synthesis of Steroid Side Chain via Stereocontrolled Protonation: Synthesis of Naturally Occurring Methyl (20S)-3β-Hydroxycholenates

Seiichi Takano, Hirotoshi Numata, Shin’ichi Yamada, Susumi Hatakeyama, and Kunio Ogasawara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Protonation of the steroidal γ-lactone enolate (10), obtained from the 20-cyano steroid (2) and (S)-benzyl 2,3-epoxypropyl ether (S-1), with saturated aqueous sodium sulfate affords the 20(R)-lactone (9a) as a major isomer which is then converted into methyl (20S)-3β-hydroxycholenates (19) and (22) isolated from a sea pen, Ptilosarcus gurneyi.