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Thesynthesisof type1 lactone stared fromtheeasilyavailable3prepared in several steps fromdihydroxyacetone.Theprotectionof thehydroxygroupwasperformedunder standard conditions using tert-butyldimethylchlorosilane (TBDMSCl)/NEt3 in DMF as solvent to afford 4 in 90%yield (Scheme 1). For the introduction of the double bond into the lactone C5 position, tert-butoxy bis(dimethylamino)methane (Brederecks reagent) was used. This reagent, which is easily made, reacted with the activated methylene group of the lactone 4. Heating Brederecks reagent and this lactone at 60 oC without solvent produced 5 in 70%yield. The enaminomoiety in 5was transformed inmoderate yield to the exomethylene double bond by reduction with NaCNBH3 under acidic

The synthesis of some unsaturated 4-substituted-g-lactones