Synthesis of (±)-Amathaspiramide F and Discovery of an Unusual Stereocontrolling Element for the [2,3]-Stevens Rearrangement

2013-10-04T00:00:00Z (GMT) by Arash Soheili Uttam K. Tambar
A 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.