Asymmetric palladium annulation: formal synthesis of (+)-huperzine A

A new formal stereoselective synthesis of (+)-huperzine A 1 was achieved using as a key step a palladium mediated annulation between 2-methylene-1,3-propanediol diacetate and (1 R,2 S)-2-phenylcyclohexanol derived β-ketoester 14. Graphic

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Bibliographic Details
Published in:Tetrahedron letters 1999-12, Vol.40 (50), p.8805-8809
Main Authors: Chassaing, Christophe, Haudrechy, Arnaud, Langlois, Yves
Format: Article
Language:English
Subjects:
alkaloids
cyclisation
palladium
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Summary:A new formal stereoselective synthesis of (+)-huperzine A 1 was achieved using as a key step a palladium mediated annulation between 2-methylene-1,3-propanediol diacetate and (1 R,2 S)-2-phenylcyclohexanol derived β-ketoester 14. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01874-2