STUDIES ON KETENE DITHIOACETALIZATION AND HYPERVALENT IODINE OXIDATION OF LUPENONE

Authors
ROY K RAJ K BHADURI AP
Citation
K. Roy et al., STUDIES ON KETENE DITHIOACETALIZATION AND HYPERVALENT IODINE OXIDATION OF LUPENONE, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 37(8), 1998, pp. 774-777
Citations number
7
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
8
Year of publication
1998
Pages
774 - 777
Database
ISI
SICI code
0376-4699(1998)37:8<774:SOKDAH>2.0.ZU;2-A
Abstract
Ketene dithioacetalization at the activated C-2 centre of triterpenic lupenone 2 has been carried out successfully to yield alpha-oxoketened ithioacetal derivative 3. Compound 3 on ring closure reactions with gu anidine hydrochloride and hydrazine hydrate famished respectively the pyrimidine and pyrazole annealed heterocycles 4-6 of lupenone. Unlike these reactions hypervalent iodine oxidation of lupenone using Koser r eagent [PhI(OH)OTs] gave various oxidised products 8-11 and did not sh ow any regiospecificity.