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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Veröffentlicht in:	Organic letters 2006-07, Vol.8 (15), p.3179-3182
Hauptverfasser:	Yu, Shanghai, Pu, Xiaotao, Cheng, Tiejun, Wang, Renxiao, Ma, Dawei
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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