Synthesis of 18,19-dihydroxycorticosterone

M. Harnik, S. Carmely, M. Cojocaru, Y. Kashman

Research output: Contribution to journalArticlepeer-review

Abstract

A four-step synthesis of 18,19-dihydroxycorticosterone 5c, starting with 19,21-dihydroxy-3,20-dioxopregn-5-ene-18,11β-lactone-di-(ethylene ketal) 2, is presented. Reduction of 2 with sodium aluminum bis-(methoxyethoxy)hydride gave 11β,18,19,21-tetrahydroxy-pregn-5-ene-3,20-dione-di-(ethylene ketal) 3a. Acetylation furnished the corresponding 18,19,21-triacetate 3b, which on treatment with a mixture of perchloric and acetic acids gave 18,19-dihydroxycorticosterone 18,19,21-triacetate 4b. Mild saponification yielded the title compound which, on the basis of ir and nmr spectra, exists as one C-20 isomer of the hemiacetal structure 5c. Periodate oxidation of 5c gave the expected 11β,19-dihydroxy-3-oxoandrost-4-ene-17β,18-carbolatone 6b.

Original languageEnglish
Pages (from-to)205-213
Number of pages9
JournalSteroids
Volume47
Issue number2-3
DOIs
StatePublished - 1986

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