The potent cytostatic agent apicularen A belongs to a growing class of macrocyclic salicylates with unique biological properties. Herein, we present a short enantioselective synthesis of side chain truncated apicularen A.
[structure: see text] A convergent, stereoselective assembly of the C1-C21 (C1'-C21') fragment of SCH 351448, a 28-membered bis-lactone natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.
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