Synthesis of (±)-amathaspiramide F and discovery of an unusual stereocontrolling element for the [2,3]-Stevens rearrangement.

doi:10.1021/ol4025937

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Synthesis of (±)-amathaspiramide F and discovery of an unusual stereocontrolling element for the [2,3]-Stevens rearrangement.

A. Soheili, U. Tambar

Sep 25, 2013

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Organic letters

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Key Takeaway

Key Takeaway: The synthesis of ()-amathaspiramide F reveals a new stereocontrolling element for [2,3]-sigmatropic rearrangements in complex molecular settings.

Abstract

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.

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