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An approach to mimicking the sesquiterpene cyclase phase by nickel-promoted diene/alkyne cooligomerization

Academic Article
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Overview

related to degree

  • Holte, Dane, Ph.D. in Chemistry, Scripps Research 2009 - 2014

authors

  • Holte, Dane
  • Gotz, D. C. G.
  • Baran, Phil

publication date

  • January 2012

journal

  • Journal of Organic Chemistry  Journal

abstract

  • Artificially mimicking the cyclase phase of terpene biosynthesis inspires the invention of new methodologies, since working with carbogenic frameworks containing minimal functionality limits the chemist's toolbox of synthetic strategies. For example, the construction of terpene skeletons from five-carbon building blocks would be an exciting pathway to mimic in the laboratory. Nature oligomerizes, cyclizes, and then oxidizes γ,γ-dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP) to all of the known terpenes. Starting from isoprene, the goal of this work was to mimic Nature's approach for rapidly building molecular complexity. In principle, the controlled oligomerization of isoprene would drastically simplify the synthesis of terpenes used in the medicine, perfumery, flavor, and materials industries. This article delineates our extensive efforts to cooligomerize isoprene or butadiene with alkynes in a controlled fashion by zerovalent nickel catalysis building off the classic studies by Wilke and co-workers.

subject areas

  • Alkynes
  • Butadienes
  • Carbon-Carbon Lyases
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Hemiterpenes
  • Molecular Mimicry
  • Molecular Structure
  • Nickel
  • Pentanes
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Identity

PubMed Central ID

  • PMC3264824

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo202314a

PubMed ID

  • 22229741
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Additional Document Info

start page

  • 825

end page

  • 842

volume

  • 77

issue

  • 2

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