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A Formal Asymmetric Synthesis of (−)-Epibatidine Using a Highly Diastereoselective Hetero Diels–Alder Reaction

✍ Scribed by Isabelle Cabanal-Duvillard; Jean-François Berrien; Léon Ghosez; Henri-Philippe Husson; Jacques Royer

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
143 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐA formal asymmetric synthesis of (2)-epibatidine is reported. The key step of the synthesis is a regio-and diastereoselective cycloaddition of silyloxycyclohexadiene with the acylnitroso dienophile derived from (1)-camphorsultam. The resulting cycloadduct was readily transformed into the N-protected-7-azabicyclo[2.2.1]heptan-2-one derivative which has previously been transformed into (2)-epibatidine.

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