DMSO MEDIATED NOVEL OXIDATIVE SKELETAL REARRANGEMENT OF RING-A IN LUPENONE

Authors
ROY K ROY R RAJ K BHADURI AP
Citation
K. Roy et al., DMSO MEDIATED NOVEL OXIDATIVE SKELETAL REARRANGEMENT OF RING-A IN LUPENONE, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 37(9), 1998, pp. 865-867
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
37
Issue
9
Year of publication
1998
Pages
865 - 867
Database
ISI
SICI code
0376-4699(1998)37:9<865:DMNOSR>2.0.ZU;2-L
Abstract
A novel one-step stereospecific synthesis of C-2-nor-1 beta-hydroxy-2- oxa-lupenone 3 is described through potassium hydroxide (KOH)-dimethyl sulphoxide (DMSO) mediated oxidation of lupenone 2. Formation of 3 is associated with an unusual oxidative skeletal rearrangement of ring-A in lupenone under the condition of oxidation.