Steroids p. 426 - 429 (1992)
Update date:2022-08-02
Topics:
Kurosawa, Takao
Ikegawa, Shigeo
Chiba, Hitoshi
Ito, Yoshito
Nakagawa, Syoichi
Kobayashi, Kunihiko
Tohma, Masahiko
18,20-Epoxy-11β,17α,20β,21-tetrahydroxypregn-4-en-3-one was synthesized by the application of hypoiodite reaction to the cortisol acetonide. The intermediary 18-iodo derivative was converted to the 11-oxo steroid by chromic acid prior to silver ion-assisted solvolysis. Removal of the protective group with hydrochloric acid was finally carried out to give the desired 11β,17α,18,21-tetrahydroxypregn-4-ene3,20-dione as the hemiacetal form. 18,20-Epoxy-11β-17α,20β,21-tetrahydroxypregna-1,4-dien-3-one was also prepared from prednisolone through a similar reaction sequence.
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Doi:10.1021/ol4013958
(2013)Doi:10.1039/c3tc30220b
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(2014)Doi:10.1002/chem.201203366
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(2013)
