10.1021/ol4025937.s006
Arash Soheili
Arash
Soheili
Uttam K. Tambar
Uttam K.
Tambar
Synthesis of (±)-Amathaspiramide F and Discovery of an Unusual Stereocontrolling Element for the [2,3]-Stevens Rearrangement
American Chemical Society
2013
substitution patterns
stereocontrolling element
Unusual Stereocontrolling Element
Stevens
rearrangement
2013-10-04 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Synthesis_of_Amathaspiramide_F_and_Discovery_of_an_Unusual_Stereocontrolling_Element_for_the_2_3_Stevens_Rearrangement/2370658
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.