ISSN:
0170-2041
Keywords:
5α-Cholest-9(II)-en-23-one, (20S,24S,25R)-3β-6α-diacetoxy-20-hydroxy-24-methyl-26-homo-
;
26-Homothornasterol B
;
Epoxy alcohol
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The absolute configuration of 3,6-di-O-acetyl-26-homothornasterol B (3) obtained previously besides the 3,6-di-O-acetyl derivative (2) of (20S,24S)-24-ethylthornasterol A by aldol reaction2a) of the mixture of (3S)-3-ethyl-4-methyl-2-(trimethylsiloxy)-1-pentene (7) and 3,4-dimethyl-2-(trimethylsiloxy)-1-hexene (8) with (+)-diacetylasterone (1) has been determined by X-ray structural analysis as (20S,24S,25R)-3β,6α-diacetoxy-20-hydroxy-24-methyl-26-homo-5α-cholest-9(11)-en-23-one. On the basis of these results a novel rearrangement and alkylation of the epoxy alcohols 6, 9, 13, and 15 with triethylaluminium have been discovered and investigated. The reaction occurs when the C-4 position adjacent to the epoxide ring is congested.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101108
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