Enantioselective Syntheses of 2-Alkyl- and 2,6-Dialkylpiperidine Alkaloids:  Preparations of the Hydrochlorides of (−)-Coniine, (−)-Solenopsin A, and (−)-Dihydropinidine

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, (−)-...

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Bibliographic Details
Published in:Organic letters 2000-01, Vol.2 (2), p.155-158
Main Authors: Wilkinson, Timothy J, Stehle, Nathan W, Beak, Peter
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Analgesics - chemical synthesis
Analgesics - chemistry
Piperidines - chemical synthesis
Piperidines - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9912534