Issue 0, 1983

Stereoselective synthesis of the plant-growth-promoting steroids dolicholide and dolichosterone

Abstract

Stereoselective syntheses of dolicholide (3), (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergost-24(28)-en-6-one, and dolichosterone (4), (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-ergost-24(28)-en-6-one, were achieved from the known (22E,24S)-2α,3α-diacetoxy-5α-stigmast-22-en-6-one (5) which is readily available from stigmasterol. The key step in the construction of the (22R,23R)-vicinal diol function in the steroidal side-chain was new and used the method of chelation control.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1983, 2133-2137

Stereoselective synthesis of the plant-growth-promoting steroids dolicholide and dolichosterone

S. Takatsuto and N. Ikekawa, J. Chem. Soc., Perkin Trans. 1, 1983, 2133 DOI: 10.1039/P19830002133

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