A highly convergent total synthesis of the antitumor antibiotic (+)-macbecin I (1) has been achieved through the homologation of the aldehyde 3 (C5-C21 aromatic fragment) to the E,Z-dienoate 2 by employing a sequential olefination strategy. Subsequent macrolactonization and a final two-step oxidation sequence were the principle steps used to complete the synthesis. Six of the seven syn-stereochemical relationships (C6-C7, C10-C11, and C14-C15) were introduced using our asymmetric crotylation bond construction methodology. The C12 stereocenter was introduced by an alkoxy-directed hydroboration reaction. An alternative strategy for introducing the C10 stereo center via a diastereoselective hydroboration reaction of 1,1-disubstituted olefin 6b provided a more atom efficient approach to intermediate 7.