[2.2.2]- to [3.2.1]-Bicycle Skeletal Rearrangement Approach to the Gibberellin Family of Natural Products

Brandon R. Smith, Jon T Njardarson

Research output: Contribution to journalArticle

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Abstract

Synthetic studies toward the gibberellin family of natural products are reported. An oxidative dearomatization/Diels-Alder cascade assembles the carbon skeleton as a [2.2.2]-bicycle, which is then transformed to the [3.2.1]-bicyclic gibberellin core via a novel Lewis acid catalyzed rearrangement. Strategic synthetic handles allow for late-stage modification of the gibberellin skeleton and provides efficient access to this important family of natural compounds.

LanguageEnglish (US)
Pages2993-2996
Number of pages4
JournalOrganic Letters
Volume20
Issue number10
DOIs
StatePublished - May 18 2018

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gibberellins
bicycle
Gibberellins
Bicycles
Biological Products
musculoskeletal system
Skeleton
products
Lewis Acids
cascades
Carbon
acids
carbon

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

[2.2.2]- to [3.2.1]-Bicycle Skeletal Rearrangement Approach to the Gibberellin Family of Natural Products. / Smith, Brandon R.; Njardarson, Jon T.

In: Organic Letters, Vol. 20, No. 10, 18.05.2018, p. 2993-2996.

Research output: Contribution to journalArticle

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