Bastimolide B (1) is a 24-membered macrolide whose structure and stereochemistry were assigned by analogy to its 40-membered ring analogue bastimolide A (C1-C39 lactone formation), which was characterized by X-ray analysis. The interest in bastimolides A and B stems from their potent antimalarial activity against multidrugresistant strains of P. falciparium. Although synthetic studies towards these natural products have been reported, there have been no total syntheses to date. Interestingly, a recent report described the use of a computer algorithm to propose a plausible route to bastimolide A in 43 steps [longest linear sequence (LLS)] using the most efficient iterative homologation reactions currently available. Herein, we describe a novel stereocontrolled approach to 1,5-polyols based on iterative boronic ester homologations and its application to the total synthesis of 1 in just 16 steps LLS. In our retrosynthetic analysis of 1, we envisioned constructing the macrocycle from terminal alkene-containing polyol 2 using (Z)-iodo crotonic acid 3 as a synthetic linchpin, which could undergo esterification followed by a stereoretentive C(sp 3 )-C(sp 2 ) Suzuki cross-coupling macrocyclization (Scheme 1A). Polyol 2 could be obtained in a convergent manner by a late-stage lithiation-borylation reaction between two equally complex fragments A (4, C24-C39) and B (5, C4-C23). These fragments would be derived from diastereo-and enantiopure poly(boronic esters) 6 and 7, respectively. Crucially, 6 and 7 could be rapidly constructed using the new hydroboration/homologation approach for the iterative assembly of 1,5-polyols, using sulfoxide 8 as the precursor of metalated TIB ester A (Scheme 1B). In addition, we reasoned that simple modification of this iterative approach by employing elongated TIB ester 9 in the homologation followed by diboration would enable construction of the alternating 1,5-and 1,3-related stereogenic centers in 7.