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The configuration of (+)-8-ethylnorlobelol-I; a correction of the literature

par Mill, Sibel ;Durant, Alex ;Hootele, Claude
Référence Liebigs Annales, 12, page (2083-2086)
Publication Publié, 1996-12

Article révisé par les pairs

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Résumé :

The piperidine alkaloid (+)-8-ethylnorlobelo-I is assigned the revised 2S,8S absolute configuration as depicted in 7. Li-Al(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. © VCH Verlagsgesellschaft mbH, 1996.