REGIOSPECIFIC SYNTHESIS OF 6-ALKYLTROPAN-2-ONES

Authors
LOMENZO SA BRADLEY AL ZHU N KLEIN CL TRUDELL MI
Citation
Sa. Lomenzo et al., REGIOSPECIFIC SYNTHESIS OF 6-ALKYLTROPAN-2-ONES, Journal of heterocyclic chemistry, 34(4), 1997, pp. 1139-1146
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
34
Issue
4
Year of publication
1997
Pages
1139 - 1146
Database
ISI
SICI code
0022-152X(1997)34:4<1139:RSO6>2.0.ZU;2-N
Abstract
A new synthetic approach for the regiospecific alkylation of the 6-pos ition of the tropane ring system has been developed, Alkylation, desul fonylation and deprotection of tropanes 5 and 12 furnished a series of 6-endo-alkyltropan-2-one derivatives 8a-e, 15a-e and 16a-e (R = Me, E t, n-Pr, n-Bu, Bn) stereoselectively in good yields. The 6-endo isomer s 15a-e and 6-exo isomers 16a-e were easily obtained as pure diastereo isomers.