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

Gallenkamp, Daniel; Fürstner, Alois

doi:10.1021/ja2031085

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

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Gallenkamp, Daniel
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Gallenkamp, D., & Fürstner, A. (2011). Stereoselective Synthesis of E,Z-Configured 1,3-Dienes by Ring-Closing Metathesis. Application to the Total Synthesis of Lactimidomycin. Journal of the American Chemical Society, 133(24), 9232-9235. doi:10.1021/ja2031085.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0025-AE91-3

Abstract

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.