TY - JOUR
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.
UR - http://www.scopus.com/inward/record.url?scp=37049113320&partnerID=8YFLogxK
U2 - 10.1039/p19800000531
DO - 10.1039/p19800000531
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AN - SCOPUS:37049113320
SN - 1470-4358
SP - 531
EP - 534
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -