Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids |
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Authors: | Hyeon Kyu Lee Jong Soo ChunChwang Siek Pak |
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Institution: | Bio-Organic Science Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yusung, Taejon 305-606, South Korea |
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Abstract: | Nonracemic 5,6-disubstituted 2-piperidones were prepared from readily accessible 3,4-disubstituted-2-azetidinones having pre-installed substituents by reductive ring opening of 2-azetidinones followed by stereoselective installation of Z-α,β-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 (+)-13 and (−)-24 were prepared from 2-azetidinones (−)-6b and (+)-18 via two-carbon ring homologation. |
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Keywords: | 2-azetidinone 2-piperidone ring homologation piperidine alkaloid |
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