Natural products Homer-Wadsworth-Emmons reaction

The Homer-Wadsworth-Emmons reaction is an important methodology used in the synthesis of natural products, but side reactions in many cases do not allow the application of this reaction in stereoselective synthesis. 

Applications of the Homer—Wadsworth—Emmons reaction to the synthesis of natural products 12COC2206. 

Recent advances in the stereoselective olefination of phosphorus-stabilized carbon nucleophiles have been reviewed. Applications of the Horner-Wadsworth-Emmons reaction to the synthesis of natural products have been highligted. A highly Z-selective synthesis of a, -unsaturated nitriles using the Homer-Wadsworth-Emmons reaction has been reported this involves a new nitrile reagent, (o-t-BuC6H40)2P(0)CH2CN, which reacts with various types of aldehydes with 86 to >99% Z selectivity. 

Kozikowski, A.P., and Sorgi, K.L., Use of the anomeric allylation reaction in natural products synthesis. A stereocontrolled synthesis of methyl deoxypseudomonate B, Tetrahedron Lett., 25, 2085, 1984. Hammond, G.B., Cox, M.B., and Wiemer, D.F., Stereocontrol in Homer-Wadsworth-Emmons condensations of a gezw-dimethylcyclopropyl aldehyde with a-substituted phosphono acetates, J. Org. Chem., 55, 128, 1990. 

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