Stereoselective Synthesis of E,Z-Configured 1,3-Dienes by Ring-Closing Metathesis. Application to the Total Synthesis of Lactimidomycin

Stereoselective Synthesis of E,Z-Configured 1,3-Dienes by Ring-Closing Metathesis. Application to the Total Synthesis of Lactimidomycin

Strategic positioning of a silyl group on the diene unit of a diene-ene substrate allows rigorous regio- and stereocontrol to be exerted during metathesis-based macrocyclization reactions. The versatility of this concise approach to E,Z-configured 1,3-dienes of ring sizes of 12 or larger is demonstr...

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Veröffentlicht in:Journal of the American Chemical Society 2011-06, Vol.133 (24), p.9232-9235
Hauptverfasser: Gallenkamp, Daniel, Fürstner, Alois
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemical synthesis
Alkenes - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Piperidones - chemical synthesis
Piperidones - chemistry
Stereoisomerism
Substrate Specificity
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Zusammenfassung:Strategic positioning of a silyl group on the diene unit of a diene-ene substrate allows rigorous regio- and stereocontrol to be exerted during metathesis-based macrocyclization reactions. The versatility of this concise approach to E,Z-configured 1,3-dienes of ring sizes of 12 or larger is demonstrated by an application to the total synthesis of lactimidomycin, a potent translation and cell-migration inhibitor.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja2031085