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Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids

✍ Scribed by Hyeon Kyu Lee; Jong Soo Chun; Chwang Siek Pak

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 249 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)01063-9

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✦ Synopsis

Nonracemic 5,6-disubstituted 2-piperidones were prepared from readily accessible 3,4-disubstituted-2-azetidinones having preinstalled substituents by reductive ring opening of 2-azetidinones followed by stereoselective installation of Z-a,b-unsaturated ester and lactam formation. For the synthetic application to the naturally occurring piperidine alkaloids, such as Prosopis and Cassia alkaloids, 5-hydroxy-2-piperidones (þ)-13 and (2)-24 were prepared from 2-azetidinones (2)-6b and (þ)-18 via two-carbon ring homologation.

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