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Synlett 1991; 1991(12): 878-880
DOI: 10.1055/s-1991-20909
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Reactions of α-Aminonitriles Under Dissolving Metal Conditions: A Concise Synthesis of (±)-Monomorine-I

Emmanuel Zeller* , David S. Grierson
  • *Institut de Chimie des Substances Naturelles, CNRS, F-91198 Gif-sur-Yvette, France
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07. März 2002 (online)

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(±)-Monomorine-I 15 (3-butyl-5-methyloctahydroindolizine) was prepared in three steps from aminonitrile 6 (2-butyl-10-cyano-5-oxa-1-azabicyclo[4.4.0]decane). This involved direct replacement of the cyano group in 6 by a methyl substituent (sodium/liquid ammonia, iodomethane), ring opening of intermediate 8 (2-butyl-10-methyl-5-oxa-1-azabicyclo[4.4.0]decane) using diethyl cyanophosphonate, and ring closure to a 1 : 2.3 mixture of 15 and the 3,8a-trans indolizidine 16 under dissolving metal conditions (potassium, 18-crown-6, tetrahydrofuran).