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Transannular Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles: total synthesis of a unique set of vinblastine analogues

Academic Article
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Overview

related to degree

  • Duncan, Katharine, Ph.D. in Chemistry, Scripps Research 2008 - 2014

authors

  • Campbell, E. L.
  • Skepper, C. K.
  • Sankar, K.
  • Duncan, Katharine
  • Boger, Dale

publication date

  • October 2013

journal

  • Organic Letters  Journal

abstract

  • A powerful tandem [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles initiated by a transannular [4 + 2] cycloaddition is detailed. An impressive four rings, four carbon-carbon bonds, and six stereocenters are set on each site of the newly formed central six-membered ring in a cascade thermal reaction that proceeds at temperatures as low as 80 °C. The resulting cycloadducts provide the basis for the synthesis of unique analogues of vinblastine containing metabolically benign deep-seated cyclic modifications at the C3/C4 centers of the vindoline-derived subunit of the natural product.

subject areas

  • Cyclization
  • Molecular Structure
  • Oxadiazoles
  • Stereoisomerism
  • Vinblastine
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/oI402549n

PubMed ID

  • 24087969
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Additional Document Info

start page

  • 5306

end page

  • 5309

volume

  • 15

issue

  • 20

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