A total synthesis of (+)-Z-deoxypukalide 3 using a combination of Stille and Nozaki–Hiyama– Kishi (NHK) coupling reactions as key steps, is described. During this study a new practical synthesis of the substituted butenolide intermediate 10, based on a combination of RCM and CM reactions from the cyclobutene ester 21 in the presence of 2-methylpropenol was also developed. Attempts to apply the intramolecular NHK reaction to the substrates 8a and 8b ...