Enantioselective syntheses of 2-alkyl- and 2,6-dialkylpiperidine alkaloids: preparations of the hydrochlorides of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine.
[reaction: see text] Sequences of lithiation-substitution, enantioselective hydrogenation, and diastereoselective lithiation-substitution provide efficient highly enantioselective syntheses of 2-substituted and cis and trans 2,6-disubstituted piperidines. The methodology is demonstrated by syntheses of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine as their hydrochlorides.
Wilkinson
T J
TJ
Department of Chemistry, University of Illinois at Urbana-Champaign, 61801, USA.
Stehle
N W
NW
Beak
P
P
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000700:Analgesics / Q000138:chemical synthesis / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000700:Analgesics; D010880:Piperidines; C409726:dihydropinidine; C002351:Solenopsin A; C007112:coniine