Reactions of α-Aminonitriles Under Dissolving Metal Conditions: A Concise Synthesis of (±)-Monomorine-I
- 1 January 1991
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1991 (12) , 878-880
- https://doi.org/10.1055/s-1991-20909
Abstract
(±)-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).Keywords
This publication has 0 references indexed in Scilit: