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

Arash Soheili, Uttam K. Tambar

Research output: Contribution to journalArticle

26 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)5138-5141
Number of pages4
JournalOrganic Letters
Volume15
Issue number19
DOIs
StatePublished - Oct 4 2013

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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