Tandem enzymatic aldol-intramolecular

A tandem enzymatic aldol-intramolecular Homer-Wadsworth-Emmons reaction has been used in the synthesis of a cyclitol.310 The key steps are illustrated in Scheme 8.33. The phosphonate aldehyde was condensed with dihydroxyacetone phosphate (DHAP) in water with FDP aldolase to give the aldol adduct, which cyclizes with an intramolecular Horner-Wadsworth-Emmons reaction to give the cyclo-pentene product. The one-pot reaction takes place in aqueous solution at slightly acidic (pH 6.1-6.8) conditions. The aqueous Wittig-type reaction has also been investigated in DNA-templated synthesis.311... 

Gijsen, H.J.M., and Wong, C.-H., Synthesis of a cyclilol via a tandem enzymatic aldol-intramolecular Horner-Wadsworth-Emmons reaction. Tetrahedron Lett., 36, 7057, 1995. 

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