Elsevier

Tetrahedron Letters

Volume 40, Issue 11, 12 March 1999, Pages 2083-2086
Tetrahedron Letters

Heck reaction of endocyclic enecarbamates with diazonium salts. Formal enantioselective syntheses of alkaloids (−)-codonopsine and (−)-codonopsinine, and the synthesis of a new C-aryl azasugar

https://doi.org/10.1016/S0040-4039(99)00151-3Get rights and content

Abstract

Formal total syntheses of the pyrrolidine alkaloids (−)-codonopsine and (−)-codonopsinine, as well as the synthesis of a new C-aryl azasugar were accomplished from a common 5-membered, enantiomerically pure endocyclic enecarbamate. The key step in those syntheses relies on a novel and practical version of the Heck reaction involving endocyclic enecarbamates and diazonium salts.

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Present address: Departamento de Química, Universidade Federal de Lavras, CEP 37200, Lavras, Mg, Brasil.

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