ol4025937_si_006.cif (16.47 kB)
Synthesis of (±)-Amathaspiramide F and Discovery of an Unusual Stereocontrolling Element for the [2,3]-Stevens Rearrangement
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posted on 2013-10-04, 00:00 authored by Arash Soheili, Uttam K. TambarA formal total synthesis of (±)-amathaspiramide F through a tandem palladium-catalyzed allylic amination/[2,3]-Stevens rearrangement is reported. The unexpected diastereoselectivity of the [2,3]-Stevens rearrangement was controlled by the substitution patterns of an aromatic ring. This discovery represents a new stereocontrolling element for [2,3]-sigmatropic rearrangements in complex molecular settings.