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Enantioselective synthesis of a key tricyclic intermediateen route to (+)-gelsemine

✍ Scribed by Jan Dijkink; Jean-Christophe Cintrat; W.Nico Speckamp; Henk Hiemstra

Book ID: 104261915
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 275 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01132-6

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✦ Synopsis

The efficient synthesis of an enantiopure Iricyclic lactam starting from (S)-5-isopropoxypyrrolin-2-one is described. The racemate of this tricyclic laetam is an intennedmte in our previously published total synthesis of racemic gelsemine, so that the present work paves the way for the synthesis of the enantiopure alkaloid. The synthetic route includes a Sonogashira coupling, a highly selective Diels-Alder reaction and a trimethylsilyl triflatemediated N-acyliminium ion cyclization as key steps.

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