The styryl-lactones are a group of secondary metabolites which have unsaturated lactone moiety in their structures. One of the most important member of this group of compound is goniothalamin. Goniothalamin and its analogs having a common -unsaturated lactone moiety. Investigations on these species have been increased in the last decade because of their interesting biological activities. Present study aims the synthesis of novel 4’-alkyl substituted klavuzon and naphthalen-1-yl substituted 3,6-dihydro-2H-pyran-2-one derivatives. Syntheses were started with the preparation of ethyl 4-(bromomethyl)-1-naphthoate. Copper-catalyzed cross coupling reactions between ethyl 4-bromoethyl-1-naphthoate and Grignard reagents gave alkyl substituted esters. Next, alkylated ester derivatives were converted to alklylated-naphthaldehyde derivatives via reduction with LiAlH4 and then oxidation with PCC. Allylation reaction of corresponding aldehydes with allylmagnesium bromide gave homoallylic alcohols. Finally, homoallylic alcohols were reacted with acryloyl chloride in the presence of a base to produce acrylate esters, then ring closing metathesis by second generation Grubbs’ catalyst yielded the final klavuzon derivatives. Additionally, synthesis of new five -unsaturated lactone derivatives was also completed. Vinylation reaction of corresponding aldehydes with vinylmagnesium bromide gave the allylic alcohols. Coupling reactions of these alcohols with 3-butenoic acid in the presence of DCC/DMAP yielded the ester. Ring closing metathesis of the related ester was studied by using 2nd generation Grubbs’ catalyst.