Castasterone (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-5α- ergostan-6-one (1) and its (22S,23S)-isomer have been synthesized from (20S)-6β-acetoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde. The side chain with the correct stereochemistry was constructed via a Claisen rearrangement and the nuclear functionalities were introduced by osmilation of the intermediate obtained by opening of the cyclopropane ring with hydrochloric acid and dehydrohalogenation.
Synthesis of castasterone and its 22S,23S-isomer: Two plant growth promoting ketones / M. Anastasia, P. Ciuffreda, M. Del Puppo, A. Fiecchi. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - (1983), pp. 383-386.
Synthesis of castasterone and its 22S,23S-isomer: Two plant growth promoting ketones
M. AnastasiaPrimo
;P. CiuffredaSecondo
;
1983
Abstract
Castasterone (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-5α- ergostan-6-one (1) and its (22S,23S)-isomer have been synthesized from (20S)-6β-acetoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde. The side chain with the correct stereochemistry was constructed via a Claisen rearrangement and the nuclear functionalities were introduced by osmilation of the intermediate obtained by opening of the cyclopropane ring with hydrochloric acid and dehydrohalogenation.
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