Journal of Organic Chemistry p. 5304 - 5309 (1982)
Update date:2022-08-04
Topics:
Eggersdorfer, Manfred L.
Kokke, W. C. M. C.
Crandell, Christopher W.
Hochlowski, Jill E.
Djerassi, Carl
A new A-nor sterol, 3β-(hydroxymethyl)-A-nor-5α-cholest-15-ene, with an unusual unsaturation in the Δ15 position has been found in the Pacific sponge Homaxinella trachys together with ten other A-nor sterols.The structure was elucidated by 360-MHz 1H NMR, 13C NMR, and mass spectral analysis as well as by chemical interconversion and comparision with synthetic 5α-cholest-15-en-3β-ol. 13C NMR spectra of the title compound and of various 3β-(hydroxymethyl)-A-nor-5α-cholestanes were assigned as an aid in future structure elucidation of this class of sterols.
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