Tetra- and hexahydro derivatives of aldosterone and 18-hydroxycorticosterone by chemical and microbial reductions

M. Harnik*, Y. Aharonowitz, R. Lamed, Y. Kashman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Preparative methods were developed for reduction with NaBH4 at 0° of 3β,5α- and 3α,5β-tetrahydroaldosterone (1) and (12) to their respective 20α-ol derivatives 2a and 13a. Corroboration of structures was obtained by periodate oxidations to the lactols 3b and 14b and thence, by further oxidation, to the lactones 4 and 15 respectively; these lactones were also independently obtained from 1 and 12. Reduction with NaBH4 at 80°C converted 1 and 12 into 18-hydroxy-3β,5α,20- and 18-hydroxy-3α,5β,20-hexahydrocorticosterone 6a and 17a respectively, which were mixtures of epimers at C-20. Compound 17a could also be prepared by reduction of the lactone 21 with sodium aluminum bis-(methoxyethoxy) hydride. Again, periodate oxidations of 6a and 17a gave the lactols 7b and 22b and thence, by Jones oxidation, the diketolactones 8 and 23. which were also prepared from 18-hydroxy-11-dehydrocorticosterone (10) and 18-hydroxycorticosterone (24) respectively. Improved conditions for reduction with Clostridium paraputrificum permitted convenient conversion of aldosterone (11), the corresponding 18 → 11 lactone 18a and 18-hydroxycorticosterone (24) into their 3α,5β-tetrahydro derivatives.

Original languageEnglish
Pages (from-to)1441-1450
Number of pages10
JournalJournal of Steroid Biochemistry
Volume19
Issue number4
DOIs
StatePublished - Oct 1983

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