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Total synthesis of kopsinine

Academic Article
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Overview

related to degree

  • Wolfe, Amanda, Ph.D. in Chemistry, Scripps Research 2008 - 2013

authors

  • Xie, J.
  • Wolfe, Amanda
  • Boger, Dale

publication date

  • February 2013

journal

  • Organic Letters  Journal

abstract

  • The use of a powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of an 1,3,4-oxadiazole in the divergent total synthesis of kopsinine (1), featuring an additional unique SmI(2)-promoted transannular cyclization reaction for formation of the bicyclo[2.2.2]octane central to its hexacyclic ring system, is detailed.

subject areas

  • Bicyclo Compounds, Heterocyclic
  • Cyclization
  • Indole Alkaloids
  • Molecular Structure
  • Octanes
  • Oxadiazoles
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC3578506

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol303573f

PubMed ID

  • 23391149
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Additional Document Info

start page

  • 868

end page

  • 870

volume

  • 15

issue

  • 4

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