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Total synthesis of (-)-vindoline and (+)-4-epi-vindoline based on a 1,3,4-oxadiazole tandem intramolecular 4+2 / 3+2 cycloaddition cascade initiated by an allene dienophile

Academic Article
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Overview

related to degree

  • Sears, Justin, Ph.D. in Chemistry, Scripps Research 2010 - 2015

authors

  • Sears, Justin
  • Barker, T. J.
  • Boger, Dale

publication date

  • 2015

journal

  • Organic Letters  Journal

abstract

  • It is reported that an allene dienophile can initiate a tandem intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles, that the intermediate cross-conjugated 1,3-dipole (a carbonyl ylide) can participate in an ensuing [3 + 2] dipolar cycloaddition in a remarkably effective manner, and that the reaction can be implemented to provide the core pentacyclic ring system of vindoline. Its discovery improves a previous total synthesis of (-)-vindoline and was used in a total synthesis of (+)-4-epi-vindoline and (+)-4-epi-vinblastine that additionally enlists an alternative series of late-stage transformations.

subject areas

  • Alkadienes
  • Cycloaddition Reaction
  • Molecular Structure
  • Oxadiazoles
  • Stereoisomerism
  • Vinblastine
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Identity

PubMed Central ID

  • PMC4636949

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/acs.orglett.5b02818

PubMed ID

  • 26457536
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Additional Document Info

start page

  • 5460

end page

  • 5463

volume

  • 17

issue

  • 21

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