STUDIES ON THE TOTAL SYNTHESIS OF NATURAL ALKALOID -(ACETYOXY)-8-AZABICYCLO[3.2.1]-OCTAN-2-EXO-OL(II) - THE SYNTHESIS OF AN INTERMEDIATE, ROXY-8-AZABICYCLO[3.2.1.]OCTANE-6-EXO-CARBONITRILE

Authors
ZENG LM YANG SM SU JY WU JQ WAN YQ
Citation
Lm. Zeng et al., STUDIES ON THE TOTAL SYNTHESIS OF NATURAL ALKALOID -(ACETYOXY)-8-AZABICYCLO[3.2.1]-OCTAN-2-EXO-OL(II) - THE SYNTHESIS OF AN INTERMEDIATE, ROXY-8-AZABICYCLO[3.2.1.]OCTANE-6-EXO-CARBONITRILE, Gaodeng xuexiao huaxue xuebao, 19(5), 1998, pp. 737-740
Citations number
8
Categorie Soggetti
Chemistry
Journal title
Gaodeng xuexiao huaxue xuebao → ACNP
ISSN journal
02510790
Volume
19
Issue
5
Year of publication
1998
Pages
737 - 740
Database
ISI
SICI code
0251-0790(1998)19:5<737:SOTTSO>2.0.ZU;2-7
Abstract
The reaction of N-methyl-3-hydroxypyridinium iodide with acrylonitrile has been studied. Under various reaction conditions, none of the desi red cycloaddition product was resulted. Instead, a Michael addition pr oduct was obtained. Alternatively, the 1,3-dipolar cycloaddition was a chieved by the reaction of N-methyl-3-oxopyridinium betaine with acryl onitrile in THF with a high regioselectivity and stereoselectivity. Th is paper reports the synthesis of an intermediate 8-methyl-2 beta-hydr oxy-8-azabicyclo [3.2.1]octane-6-exo-carbonitrile of exo-(acetyoxy)-8- azabicyclo[3.2.1]-octan-2-exo-ol. This synthetic route involves two hi gh stereoselective steps.