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Decarbonylation of α-tertiary amino acids application to the synthesis of polyhydroxylated indolizidines from D,L-pipecolic acid

✍ Scribed by María J. Martín-López; Rosa Rodriguez; Francisco Bermejo

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 821 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00689-9

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✦ Synopsis

The decarbonylation of the bicyclic a-tertiary carboxamido acid 11 led to the enamide 12, easily transformed into the indolizidine alkaloid 8,8a-trans-8-hydroxy-indolizidine 14. Likewise, the same process applied to the ¢t-substituted pipecolic acid derivative 5 led to the unsaturated ester 6 which was easily transformed either into ~-coniceine 9 or to 14. The thermal fragmentation of the acyl derivative 22 led to the enamide 24 which has been transformed into (+)-swainsonine 26.

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