Scyphostatin, which was isolated from Dasyscyphus mollissimus SANK-13892 in 1997, is a lead compound for the treatment of inflammation and autoimmune desease for its potent activity inhibiting a neutral sphingomyelinase. But it is very unstable compound, which consists of highly substituted cyclohexane core with aminoalcohol unit and unsatuated fatty acid. We report herein regio and stereoselective asymmetric synthesis of scyphostatin from the chiral cyclohexane acetal obtained by an intramoleucular bromoetherification of σ-symmetric cyclohexadiene acetal, prepared from chiral hydrobenzoin.
