Total synthesis of (−)-desoxoprosopinine via the diastereoselective reduction of homochiral2-Acyl-N-Boc-oxazolidines

✍ Scribed by Claude Agami; François Couty; Hélène Mathieu

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 213 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)00646-7

✦ Synopsis

Desoxoprosopinine was synthesised fi'om (R)-phenylglycinol as the chiral source. The three distinct steps used for the construction of the three stereogenic centers of the target were all highly diastereoselective. These steps include a reduction ofa homochiml N-Boc-2-acyl oxazolidine and the stereoselectivity of this reaction can be explained by a non chelated model. An original N-debenzylation of the phenyl glycinol appendage was devised in this synthesis.