Tetrahedron

… piperideines—IX11For Part VIII in this series see: M. Bonin, R. Besselièvre, DS Grierson and H.-P. Husson, Tetrahedron Letters, 1493,(1983).: General strategies for …

DS Grierson, M Harris, HP Husson

Index: Grierson, David S.; Harris, Martin; Husson, Henri-Philippe Tetrahedron, 1983 , vol. 39, # 22 p. 3683 - 3694

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Abstract

The syntheses of three Corynanthé-Strychnos type indole systems illustrate how 2-cyano Δ3 piperideines 1 can be used as synthons for a general approach to the construction of complex alkaloids. By condensation of amino-nitrile 23 with sodium dimethylmalonate and subsequent deprotection of indole N and ring closure in HCl/MeOH, the cis indoloquinolizidine 16a was prepared in 45% overall yield. The reaction of 2-cyano-Δ3- ...