Abstract: A procedure has been developed for the coupling of acetals 4-7 derived from (R, R)-2, 4-pentanedioI with a-silyl ketones or enol silyl ethers to give aldol ethers 8/9 in excellent yield and high diastereoselectivity, 8: 9=> 95: 5. This methodology has been applied to a total asymmetric synthesis of (2S, 4R)-2, 4-dihydroxyoct-7-ene, a key intermediate in the Bartlett synthesis of nonactic acid.
