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Synlett 1991; 1991(12): 878-880
DOI: 10.1055/s-1991-20909
DOI: 10.1055/s-1991-20909
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Reactions of α-Aminonitriles Under Dissolving Metal Conditions: A Concise Synthesis of (±)-Monomorine-I
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Publikationsdatum:
07. März 2002 (online)
![](https://www.thieme-connect.de/media/synlett/199112/lookinside/thumbnails/10.1055-s-1991-20909-1.jpg)
(±)-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).