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Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate

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Authors
Mihailović, Mihailo Lj.
Dabović, Milan
Pavlović, Vladimir D.
Krstić, Natalija
Lorenc, Ljubinka
Article (Published version)
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Abstract
5-Hydroxy-5α-cholest-8-en-3β-yl acetate (8) (prepared in 6 steps starting from 7-dehydrocholesteryl acetate (1) was transformed with ruthenium tetroxide to 5-hydroxy-8,9-dioxo-8,9-seco-5α-cholestan-3β-yl acetate (9). Treatment of the latter 8,9-seco-5-hydroxy derivative with lead tetraacetate (LTA) or mercuric oxide/iodine reagent (HgO/I2) resulted, instead of the expected oxidative β-fragmentation of its C(5)-C(10) bond, in the competing non-regio and non-stereoselective acetoxylation of the α-positions next to the 8- and 9-oxo functions (with LTA), and in the ≈ 82% recovery of the starting material (with HgO/I2). The results are discussed in terms of the strong hydrogen bonding which exists between the 5α-hydroxyl and the 8-oxo group.
Keywords:
Lactones / Acetates / secosteroidal macrocycles
Source:
Journal of the Serbian Chemical Society, 1997, 62, 9, 719-726
Publisher:
  • Serbian Chemical Society

ISSN: 0352-5139

Scopus: 2-s2.0-0038979692
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2707
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IHTM

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