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Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: application to the synthesis of (-)-sedamine.

ABSTRACT: Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield.

SUBMITTER: Zheng G

PROVIDER: S-EPMC3597091 | biostudies-literature | 2004 Nov

REPOSITORIES: biostudies-literature

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Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: application to the synthesis of (-)-sedamine.

Zheng Guangrong G Dwoskin Linda P LP Crooks Peter A PA

The Journal of organic chemistry 20041101 24

Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield. ...[more]

PMID: 15549833

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