Conversion of the allylic and homoallylic steroidal alcohols to the corresponding saturated ketones by means of the activated Ra/Ni

Forsek, J.

doi:10.1016/s0040-4039(00)78842-3

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Cited by 11 publications

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“…30% overall yield from 1 . This modest but easily reproducible yield of 7 was sufficient for our purposes because of the easy availability of coprostanone by the Raney nickel-catalyzed isomerization of cholesterol …”

Section: Resultsmentioning

confidence: 99%

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The Supertristeroids: Large, Chiral, Molecular Bowls Prepared by Trimerization of Pentacyclic Steroidal Ketones

Song

Pascal

2007

J. Org. Chem.

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Robinson annulation of coprostanone (1) at the 2,3- and 3,4-positions gave two pentacyclic enones (7 and 10) that contain A/B-cis-fused ring junctions. Reduction of these enones gave the pentacyclic steroidal ketones 2 alpha,3beta- (8) and 2 alpha,3 alpha-(3'-oxocyclohexano)-5 beta-cholestane (9) and 4 alpha,3beta- (11) and 4 alpha,3 alpha-(3'-oxocyclohexano)-5 beta-cholestane (12). The structures of compounds 8, 9, and 11 were unambiguously established by X-ray analysis. TiCl4-promoted trimerization of compounds 8 and 11 gave the "supertristeroids" 4 and 5, respectively: large (C93) chiral, hydrocarbon clefts with C3-symmetric pockets approximately 12 A in diameter.

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Section: Resultsmentioning

confidence: 99%

“…Coprostanone (5β-cholestan-3-one), mp 56−58 °C (lit . 60−61 °C) was prepared by the method of Forsek …”

Section: Methodsmentioning

confidence: 99%