Four possible stereoisomers of 3-hydroxy-4-methyltetradecanoic acid were enantioselectively synthesized by using Sharpless epoxidation and a subsequent epoxide-ring opening reaction with trimethylaluminum as the key steps. The absolute configuration of the beta-oxyacid component of antifungal cyclodepsipeptides W493 A and B was consequently determined as 3S,4R.
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Nihei et al. (2005) studied this question.
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