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Regioselective ring-closing metathesis on terpenoid acrylates and acrylamides
Journal article   Peer reviewed

Regioselective ring-closing metathesis on terpenoid acrylates and acrylamides

Yanming Du and David F Wiemer
Tetrahedron letters, Vol.42(35), pp.6069-6072
2001
DOI: 10.1016/S0040-4039(01)01179-0

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Abstract

A series of acrylate esters was prepared by treatment of representative terpenoid aldehydes with allyl or vinyl magnesium bromide followed by reaction with acryloyl chloride. In all cases, ring-closing metathesis (RCM) resulted in regioselective formation of unsaturated lactones through metathesis of the acrylate and terminal olefins. After condensation of farnesal with a primary amine, a parallel series of reactions led to formation of the corresponding lactam. Graphic

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