Photo-induced transformations. Part LXI. Syntheses of some six-membered and eight-membered lactams of theB-homo- andA-nor-B,B-dihomocholestane series by the photo-Beckmann rearrangement
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 931-938
- https://doi.org/10.1039/p19820000931
Abstract
The syntheses of 3-aza-B-homo-5α-cholestan-4-one, 4-aza-B-homo-5α-cholestan-3-one, 6-aza-A-nor-B,B-dihomo-5α- and 5β-cholestan-7-one, and 7-aza-A-nor-B,B-dihomo-5α- and 5β-cholestan-6-one by the photo-Beckmann rearrangement of the oximes of A-nor-B-homo-5α-cholestan-3-one and A-nor-B-homo-5α and 5β-cholestan-6-one are described. An A/Btrans ring-junction stereochemistry of the parent ketones was deduced by estimating the relative stabilities of the principal conformers of the A/Bcis- and trans-isomers of the A-nor-B-homocholestan-3-ones and A-nor-B-homocholestan-6-ones by molecular mechanics calculations.Keywords
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