Asymmetric Synthesis via Acetal Templates. 10. Aldol-Type Reactions. Preparation of a Nonacetic Acid Intermediate

W Johnson, C Edington, J Elliot…

Index: Johnson; Elliott; Hanson Journal of the American Chemical Society, 1984 , vol. 106, # 4 p. 1138 - 1139

Full Text: HTML

Citation Number: 47

Abstract

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.