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An Efficient Enantioselective Entry to the Piperidino‐Quinolizidine Ring System of Lupine Alkaloids by Means of N ‐Acyliminium Ion Initiated Cyclization Reactions
Author(s) -
Consonni Alessandra,
Danieli Bruno,
Lesma Giordano,
Passarella Daniele,
Piacenti Paola,
Silvani Alessandra
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200104)2001:7<1377::aid-ejoc1377>3.0.co;2-f
Subject(s) - quinolizidine , enantioselective synthesis , chemistry , indolizidine , stereochemistry , stereoselectivity , ring (chemistry) , alkaloid , nonane , iminium , organic chemistry , ion , catalysis
Abstract An efficient methodology for the enantioselective synthesis of the decahydro‐1,5‐methano‐pyrido[1,2‐ a ][1,5]diazocine skeleton found in tricyclic lupine alkaloids is described, starting from 3,5‐disubstituted piperidines as chiral building blocks. Alkyne‐ or vinylsilane‐terminated N ‐acyliminium ion cyclizations performed on appropriate 3,7‐diazabicyclo[3.3.1]nonane derivatives allow for the highly stereoselective construction of piperidino‐quinolizidine ring systems. A preliminary application of this methodology results in the synthesis of the quinolizidine alkaloid virgilidone.