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

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

doi:10.1039/p19800000531

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

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

Weizmann Institute of Science
Hebrew University of Jerusalem

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	531-534
Number of pages	4
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/p19800000531
State	Published - 1980
Externally published	Yes

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

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.",

author = "Isaac Kirson and Gideon G{\"u}nzberg and Gottlieb, \{Hugo E.\} and Erwin Glotter",

year = "1980",

doi = "10.1039/p19800000531",

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journal = "Journal of the Chemical Society, Perkin Transactions 1",

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T1 - Acid-catalysed dehydration of withanolide E, a 14α, 17β, 20αF-trihydroxysteroid; a revision

AU - Kirson, Isaac

AU - Günzberg, Gideon

AU - Gottlieb, Hugo E.

AU - Glotter, Erwin

PY - 1980

Y1 - 1980

N2 - 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.

AB - 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.

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ER -

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

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