Multi-gram-scale synthesis of a versatile syn-anti stereotriad by a short and cost-effective route

Abstract

The polyketide family of natural products includes numerous biologically important molecules that exhibit a variety of complex structures. The biosynthesis of these diverse structures relies on the iterative assembly of individual segments controlled by the enzymes of the polyketide synthase (PKS) family. In the synthesis laboratory, access to stereospecifically-prepared ketide building blocks can be both challenging and costlimiting. We report an efficient, multigram-scale synthesis of the syn-anti synthon (2S,3R,4S)(E)-6-cyclohexyl-3-[(4-methoxybenzyl)oxy]-2,4-dimethylhex-5-en-1-ol from the commercially available cyclohexanecarboxaldehyde in excellent overall yield and purity.