A formal asymmetric synthesis of (-)-epibatidine using a highly diastereoselective hetero Diels-Alder reaction
(2000) Tetrahedron — Vol. 56, n° 23, p. 3763-3769 (2000)
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- A formal asymmetric synthesis of (-)-epibatidine is reported. The key step of the synthesis is a regio- and diastereoselective cycloaddition of silyloxycyclohexadiene with the acylnitroso dienophile derived from (+)-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 (-)-epibatidine. (C) 2000 Elsevier Science Ltd. All rights reserved.
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Cabanal-Duvillard, I., Berrien, J.-F., Ghosez, L., Husson, H.-P., & Royer, J. (2000). A formal asymmetric synthesis of (-)-epibatidine using a highly diastereoselective hetero Diels-Alder reaction. Tetrahedron, 56(23), 3763-3769. https://doi.org/10.1016/S0040-4020(00)00284-2 (Original work published 2000)