ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Upon heating in AcOH, the stereoisomeric (Z)- and (R)-6,9-dioxocyclodex-3-enyl derivatives, 5 and 6, respectively, obtained by HgO/I2 oxidation of 5-hydroxy-8-oxo-8,14-seco-5α-androstane-3β,17β-diyl diacetate (3), undergo an unusual intramolecular rearrangement to give the corresponding unsaturated (5R,9R)- and (5R,9S)-spiro-lactones 7 and 8, respectively. Hydroxylation of the C=C bond in 7 and 8, and subsequent glycol cleavage of the resulting diols 9 and 10 afforded the epimeric spiro-lactones (5R,9S)-11 and (5R,9R)-14, respectively, and in both cases, the ring-D-containing fragments 12 and 13.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19950780412
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