Journal
TETRAHEDRON
Volume 58, Issue 1, Pages 61-74Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)01138-3
Keywords
stemonamide isostemonamide; acyliminium; aldol spirocyclization; Mannich reaction
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Two different approaches to the alkaloids stemonamide and isostemonamide using N-acyliminium chemistry are described. The approach using an aldol spirocyclization to construct the second contiguous spirocenter was successful. The total synthesis of these products was completed by 1,4-addition of an appropriate side chain, alpha -methylenation by Mannich reaction, double bond isomerization and closure of the azepine ring. (C) 2002 Elsevier Science Ltd. All rights reserved.
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