A formal, stereoselective synthesis of Aspergillide‐B is described. A highly diastereoselective Pd(0)‐B(OPh)3 mediated syn‐vic‐diol formation from epoxy unsaturated ester used for the creation of C3‐C4 centres. Iodine catalyzed allylation used for synthesis of trans‐2,6‐disubstitutedtetrahydro‐2H‐Pyran. Cross‐ metathesis, Yamaguchi macrolactonization are the other key features of the synthesis.