Total Synthesis of Clavepictines A and B and Pictamine

A short route for assembling clavepictines A and B and pictamine is described, which features elaboration of its trisubstituted piperidine moiety via condensation of a β-keto sulfone with an l-alanine-derived bromide and subsequent alkylative cyclization and construction of its quinolizidine skeleto...

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Bibliographic Details
Published in:Organic letters 2006-07, Vol.8 (15), p.3179-3182
Main Authors: Yu, Shanghai, Pu, Xiaotao, Cheng, Tiejun, Wang, Renxiao, Ma, Dawei
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Animals
Crystallography, X-Ray
Heterocyclic Compounds, 2-Ring - chemical synthesis
Molecular Conformation
Molecular Structure
Quinolizines - chemical synthesis
Stereoisomerism
Urochordata - chemistry
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Summary:A short route for assembling clavepictines A and B and pictamine is described, which features elaboration of its trisubstituted piperidine moiety via condensation of a β-keto sulfone with an l-alanine-derived bromide and subsequent alkylative cyclization and construction of its quinolizidine skeleton via a diastereoselective intramolecular conjugate addition. The possible stereochemical course for this conjugate addition is discussed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol060960b