Development of Ferrier(II) Carbocyclization Catalyzed by Pd(II) and Its Application to the Synthesis of Bioactive Substances

摘要

Highly functionalized cyclohexanes are useful intermediates for the synthesis of natural products and their derivatives having 6-membered ring systems. Among the preparation of chiral substituted cyclohexanes. Hg(II) salts mediated conversion of aldohexoses into cyclohexanones [Ferrier (II) carbocyclization] has become one of the most efficient and intriguing process. This article summarizes our recent works concerning the development of the catalytic Ferrier(II) carbocyclization mediated by Pd(II) salts and the application of this reaction to the total syntheses: i) #beta#-glucosidase inhibitor, cyclophellitol, ii) all diastereoisomers of inositol and D-myo-inositol phosphates. It should be emphasized that PdCl_2-mediated transformation enabled us to prepare such expensive inositol derivatives efficiently.