Acid-catalysed dehydration of withanolide E, a 14α, 17β, 20αF-trihydroxysteroid; a revision

Isaac Kirson, Gideon Günzberg, Hugo E. Gottlieb, Erwin Glotter

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The structure of the products obtained by treatment of (17S, 2OS, 22R)-5β, 6β-epoxy-14α, 17, 20-trihydroxy-1-oxowitha-2, 24-dienolide (withanolide E) with sulphuric acid in acetone solution has been reinvestigated. Whereas the major component is indeed (17S, 20S, 22R)-5α, 6β, 17, 20-tetrahydroxy-1-oxowitha-2, 14, 24-trienolide, the minor component which was previously considered to be the Δ8(11) isomer of the latter, has now been shown to be (17S, 22R), 14α, 20ξ-epoxy-5α, 6β, 17-trihydroxy-1-oxowitha-2, 24-dienolide. The configuration at C-20 is most probably 20R.

Original languageEnglish
Pages (from-to)531-534
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
StatePublished - 1980
Externally publishedYes

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