ISSN:
0947-3440
Keywords:
Cycloaddition, 1,3-dipolar
;
Piperidine
;
Alkaloids
;
Lobelia
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The piperidine alkaloid (+)-8-ethylnorlobelo-I is assigned the revised 2S,8,S absolute configuration as depicted in 7. LiAl(O-tBu)3H reduction of the ketone rac-5 proceeded with a high stereoselectivity to give, after hydrolysis of the carbamate function, the syn amino alcohol rac-6. Inversion of the C-8 configuration of ent-6 yielded (-)-8-ethylnorlobelol-I ent-7. A short nitrone-alkene-based synthesis of rac-7 has been developed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961220
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