Synthesis of des-A-B-secocholestanes
Two independent synthetic routes to 10-oxo-5, 10-seco-des-A-cholestan-5-oic acid ( 5 ) are described. The route including the Baeyer-Villiger rearrangement of (10R)-des-A-cholestan-5-one ( 2 a), followed by hydrolysis of the lactone 3 a obtained and oxidation of the C-10 hydroxyl group, seems to be...
Gespeichert in:
Veröffentlicht in: | Canadian journal of chemistry 1984-06, Vol.62 (6), p.1081-1084 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | Two independent synthetic routes to 10-oxo-5, 10-seco-des-A-cholestan-5-oic acid (
5
) are described. The route including the Baeyer-Villiger rearrangement of (10R)-des-A-cholestan-5-one (
2
a), followed by hydrolysis of the lactone
3
a obtained and oxidation of the C-10 hydroxyl group, seems to be superior to ozonolysis of the 5(10)-enol acetate
6
of des-A-ketone which resulted in the formation of 5,10-seco-des-A-19-norcholestan-5,10-dioic acid (
7
), in addition to the compound
5
. Product
7
and its 6-nor analog
12
have also been obtained by ruthenium tetroxide oxidation of the respective A-ring phenols
8
,
9
, and
11
. |
---|---|
ISSN: | 0008-4042 1480-3291 |
DOI: | 10.1139/v84-178 |