The Configuration of (+)-8-Ethylnorlobelol-I; a Correction of the Literature

✍ Scribed by Mill, Sibel ;Durant, Alex ;Hootelé, Claude

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 399 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619961220

✦ Synopsis

Abstract

The piperidine alkaloid (+)‐8‐ethylnorlobelo‐I is assigned the revised 2__S__,8,S absolute configuration as depicted in 7. LiAl(O‐__t__Bu)~3~H 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.