1-(2-Pyridyl)-2-propen-1-ol, obtained by vinylation of commercially available picolinaldehyde, resulted a good starting material for the synthesis of the indolizidine skeleton. In particular, a simple process involving bromination, reduction, and nucleophilic substitution (via elimination and addition) allowed an easy conversion of the starting material into (±)-lentiginosine in ∼27% overall yield.

Synthesis of 1,2-dihydroxyindolizidines from 1-(2-pyridyl)-2-propen-1-ol / D. Giomi; R. Alfini; A. Micoli; E. Calamai; C. Faggi; A. Brandi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 76:(2011), pp. 9536-9541. [10.1021/jo201830b]

Synthesis of 1,2-dihydroxyindolizidines from 1-(2-pyridyl)-2-propen-1-ol

GIOMI, DONATELLA;ALFINI, RENZO;FAGGI, CRISTINA;BRANDI, ALBERTO
2011

Abstract

1-(2-Pyridyl)-2-propen-1-ol, obtained by vinylation of commercially available picolinaldehyde, resulted a good starting material for the synthesis of the indolizidine skeleton. In particular, a simple process involving bromination, reduction, and nucleophilic substitution (via elimination and addition) allowed an easy conversion of the starting material into (±)-lentiginosine in ∼27% overall yield.
2011
76
9536
9541
D. Giomi; R. Alfini; A. Micoli; E. Calamai; C. Faggi; A. Brandi
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/538256
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