RESUMEN
A new chiral sulfinyl transfer auxiliary derived from readily available phenylglycine was developed. This auxiliary is utilized to synthesize a diverse array of alkyl- and arylsulfinamides and sulfinylferrocenes in high yields and excellent ee's. The desired products are produced in a one-pot sequence from the oxathiazolidine 2-oxide by two sequential nucleophilic additions that proceed in a stereospecific manner.
Asunto(s)
Amidas/síntesis química , Compuestos Ferrosos/síntesis química , Glicina/química , Compuestos de Sulfhidrilo/síntesis química , Amidas/química , Compuestos Ferrosos/química , Glicina/análogos & derivados , Metalocenos , Estructura Molecular , Estereoisomerismo , Compuestos de Sulfhidrilo/químicaRESUMEN
The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C.
