Stereoselectivity of electrophile-promoted cyclizations of. gamma.-hydroxyalkenes. An investigation of carbohydrate-derived and model substrates

…, BE Maryanoff, D Liotta, R Monahan III

Index: Reitz, Allen B.; Nortey, Samuel O.; Maryanoff, Bruce E.; Liotta, Dennis; Robert, Monahan Journal of Organic Chemistry, 1987 ,  vol. 52,  # 19  p. 4191 - 4202

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Citation Number: 91

Abstract

We have investigated cyclization reactions of y-hydroxyalkenes bearing an alkoxy or alkyl substituent on the allylic carbon. A variety of electrophiles [N-bromosuccinimide, N- iodosuccinimide, iodine, mercury (I1) acetate, mercury (I1) trifluoroacetate, mercury (I1) triflate, benzeneselenenyl chloride, and N-(phenylseleneny1) phthalimidel were employed. Alkenol 5 was prepared from D-arabinose and methylenetriphenylphosphorane, and ...