Development of Synthetic Methodologies for Acyclic Organic Molecules Having Multi-Chiral Centers and Their Application to Natural Product Synthesis

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Development of highly stereoselective synthetic methodologies for acyclic organic molecules having contiguous asymmetric centers is one of the important research projects in modern synthetic organic chemistry in context with the chiral synthesis of biologically and medicinally important compounds. This research project was carried out aiming at the development of highly stereoselective synthetic methodologies for acyclic organic molecules having contiguous asymmetric centers using stereospecific substitution reactions of epoxides as synthetic strategy .when this grant was provided.(1) The C2 selective alkyl and alkynyl substitution reactions of 2,3-epoxy alcohols by the use of organoaluminum ate complexes.(2) Novel and powerful reagent system for stereospecific alkylation-silylation reactions of epoxides.(3) A regio- and stereoselective a-methylation of γ, δ-epoxy-α, β-unsaturated esters with a Me_2Zn-CuCN reagent.(4) Stereospecific acyclic stereocontrol with double inversion of the configuration.(5) The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates.(6) Stereoselective total synthesis of PM Toxin A, a corn Host-Specific Pathotoxins.(7) Total Synthesis of Ingenol.(8) Stereoselective total synthesis of zincophorin, the unique ionophore antibiotic.