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Total synthesis of (+)-fendleridine (aspidoalbidine) and (+)-1-acetylaspidoalbidine

Academic Article
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Overview

related to degree

  • Zuhl, Andrea M., Ph.D. in Chemistry, Scripps Research 2006 - 2012

authors

  • Campbell, E. L.
  • Zuhl, Andrea M.
  • Liu, C. M.
  • Boger, Dale

publication date

  • March 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A total synthesis of the Aspidosperma alkaloids (+)-fendleridine and (+)-1-acetylaspidoalbidine is detailed, providing access to both enantiomers of the natural products and establishing their absolute configuration. Central to the synthetic approach is a powerful intramolecular [4+2]/[3+2] cycloaddition cascade of a 1,3,4-oxadiazole in which the pentacyclic skeleton and all the stereochemistry of the natural products are assembled in a reaction that forms three rings, four C-C bonds, and five stereogenic centers including three contiguous quaternary centers, and introduces the correct oxidation state at C19 in a single synthetic operation. The final tetrahydrofuran bridge is subsequently installed in one step, enlisting an intramolecular alcohol addition to an iminium ion generated by nitrogen-assisted opening of the cycloadduct oxido bridge, with a modification that permits release of useful functionality (a ketone) at the cleavage termini.

subject areas

  • Aspidosperma
  • Cyclization
  • Indole Alkaloids
  • Molecular Conformation
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2832086

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja908819q

PubMed ID

  • 20148585
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Additional Document Info

start page

  • 3009

end page

  • 3012

volume

  • 132

issue

  • 9

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