- An efficient enantioselective entry to the piperidino-quinolizidine ring system of lupine alkaloids by means of n-acyliminium ion initiated cyclization reactions
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An efficient methodology for the enantioselective synthesis of the decahydro-1,5-methano-pyrido[1,2-α][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.
- Consonni, Alessandra,Danieli, Bruno,Lesma, Giordano,Passarella, Daniele,Piacenti, Paola,Silvani, Alessandra
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p. 1377 - 1383
(2007/10/03)
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