TOTAL SYNTHESIS AND DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF EPIBATIDINE

Authors
FLETCHER SR BAKER R CHAMBERS MS HERBERT RH HOBBS SC THOMAS SR VERRIER HM WATT AP BALL RG
Citation
Sr. Fletcher et al., TOTAL SYNTHESIS AND DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF EPIBATIDINE, Journal of organic chemistry, 59(7), 1994, pp. 1771-1778
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
7
Year of publication
1994
Pages
1771 - 1778
Database
ISI
SICI code
0022-3263(1994)59:7<1771:TSADOT>2.0.ZU;2-0
Abstract
The synthesis of (+)- and (-)-epibatidine (exo-2-(2-chloropyridin-5-yl )-7-azabicyclo [2.2.1]heptane) via reaction of 5-lithio-2-chloropyridi ne with (+)- and (-)-N-BOC-7-azabicyclo[2.2.1]heptan-2-one is describe d. The absolute configuration of the natural product is shown to be 1R ,2R,4S.