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

Brandon R. Smith; Jon T. Njardarson

doi:10.1021/acs.orglett.8b01031

[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 journal › Article › peer-review

9 Scopus citations

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.

Original language	English (US)
Pages (from-to)	2993-2996
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.8b01031
State	Published - May 18 2018
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b01031

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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.",

author = "Smith, {Brandon R.} and Njardarson, {Jon T.}",

note = "Funding Information: Financial support was provided by The University of Arizona and the National Science Foundation (CHE-1266365). Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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AU - Njardarson, Jon T.

PY - 2018/5/18

Y1 - 2018/5/18

N2 - 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.

AB - 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.

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

Abstract

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CCDC 1821698: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1821698: Experimental Crystal Structure Determination

Cite this