SYNTHESIS OF ,3-BIS(ACETOXYMETHYL)BICYCLO[2.2.1]HEPTA-2,5-DIENE AND ITS USE IN PALLADIUM-CATALYZED ELIMINATION

Authors
MUCHOW G BRUNEL JM MAFFEI M BUONO G
Citation
G. Muchow et al., SYNTHESIS OF ,3-BIS(ACETOXYMETHYL)BICYCLO[2.2.1]HEPTA-2,5-DIENE AND ITS USE IN PALLADIUM-CATALYZED ELIMINATION, Journal of organic chemistry, 60(4), 1995, pp. 852-855
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
4
Year of publication
1995
Pages
852 - 855
Database
ISI
SICI code
0022-3263(1995)60:4<852:SO,AI>2.0.ZU;2-J
Abstract
The synthesis of a novel polyfunctional bicyclic compound, ,3-bis(acet oxymethyl)bicyclo[2.2.1]hepta-2,5-diene (1), is reported. The obtained prochiral synthon may be considered as a useful substrate on the rout e toward natural products and compounds of pharmaceutical interest. Su bmission of 1 to palladium-catalyzed elimination affords vinylic aceta te 3, ethylene-3-(acetoxyvinyl)bicyclo[2.2.1]hept-5-ene, in excellent yields.