Enantioselective syntheses of 2-alkyl- and 2,6-dialkylpiperidine alkaloids: Preparations of the hydrochlorides of (-)coniine, (-)-solenopsin A, and (-)-dihydropinidine

Authors
Wilkinson, TJ Stehle, NW Beak, P
Citation
Tj. Wilkinson et al., Enantioselective syntheses of 2-alkyl- and 2,6-dialkylpiperidine alkaloids: Preparations of the hydrochlorides of (-)coniine, (-)-solenopsin A, and (-)-dihydropinidine, ORG LETT, 2(2), 2000, pp. 155-158
Citations number
54
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
2
Year of publication
2000
Pages
155 - 158
Database
ISI
SICI code
1523-7060(20000127)2:2<155:ESO2A2>2.0.ZU;2-X
Abstract
[GRAPHICS] Sequences of lithiation-substitution, enantioselective hydrogenation, and d iastereoselective lithiation-substitution provide efficient highly enantios elective syntheses of 2-substituted and cis and trans 2,6-disubstituted pip eridines. The methodology is demonstrated by syntheses of (-)-coniine, (-)- solenopsin A, and (-)-dihydropinidine as their hydrochlorides.