Development of Novel Carbanion Rearrangements as a Stereoselective Approach toward Heteroatom-containing Natural Products

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The following novel carbanion reactions of hetero-functionalized system have been developed.I.Oxy systema)Ring-enlarging [2,3]-Wittig rearrangement of cyclic acetals : Stereoselective approach to medium-sized cyclic vinyl ethers.b)Ring-contracting [1,2]-Wittig rearrangement of cyclic acetals : Stereoselective approach to medium-sized cyclic ethers.c)Anionic ring-contraction reaction of cyclic acetal system : Stereoselective approach to multi-functionalized oxetanes.d)[1,4]-Wittig rearrangement containing ethynylvinylmethanol-derived migration terminus : Tandem rearrangement-aldol reaction.II.Aza systema)Ring-enlarging aza-[1,2] and [2,3]-rearrangement of cyclic hemiaminals.b)Asymmetric aza-Wirtig rearrangement induced by Sn-Li transmetalation.c)The sequential carbanion reactions of phthalimide-derived alkynyl hemiaminal: Efficient approach to polysubstituted pyrrole via four components coupling.d)Stevens rearrangement of a cyclic hemiacetal system: Diastereoselective approach to chiral α-amino ketone.