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Asymmetric synthesis of highly functionalized tetracyclic indole bases embodying the basic skeleton of yohimbine- and reserpine type alkaloids

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Lock, R., & Waldmann, H. (1996). Asymmetric synthesis of highly functionalized tetracyclic indole bases embodying the basic skeleton of yohimbine- and reserpine type alkaloids. TETRAHEDRON LETTERS, 37(16), 2753-2756. doi:10.1016/0040-4039(96)00388-7.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-71FB-A
Abstract
Schiff bases derived from tryptophan methyl ester react with differently substituted electron-rich siloxy dienes in the presence of achiral or chiral boric acid esters to give enaminones 5 and 6 with high diastereomer ratios (up to >98:2). These intermediates are converted into highly functionalized indoloquinolizines 14 and 15 by means of a new method which employs the transformation of vinylogous amides to vinylogous chloromethyl amines and their subsequent conversion to vinylogous imidoyl chlorides as the key step. Copyright (C) 1996 Elsevier Science Ltd.