REACTIONS OF DIENES WITH SELENIUM DIOXIDE .3. SELENOLABDANES FROM METHYL 15-O-ACETYLISOCUPRESSATE

Authors
MEDARDE M LOPEZ JL IRIBAR J FELICIANO AS CARPY A LEGER JM
Citation
M. Medarde et al., REACTIONS OF DIENES WITH SELENIUM DIOXIDE .3. SELENOLABDANES FROM METHYL 15-O-ACETYLISOCUPRESSATE, Tetrahedron, 51(40), 1995, pp. 11011-11020
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
40
Year of publication
1995
Pages
11011 - 11020
Database
ISI
SICI code
0040-4020(1995)51:40<11011:RODWSD>2.0.ZU;2-X
Abstract
The reaction of methyl 15-O-acetylisocupressate with SeO2/MeOH yielded , in addition to the expected products of allylic oxidation, approxima te to 20% of selenepanes and selenocanes. The formation of cyclic sele nium compounds from diolefins in this reaction is similar to that obse rved from acetyllinalool. The mechanistic proposal through a double el ectrophilic attack to both double bonds explains the structural variat ion of the selenium containing products in this and in previous cases.