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Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: Total synthesis of acremoauxin A and oxazinin 3

Academic Article
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Overview

related to degree

  • Lin, David Wei, Ph.D. in Chemistry, Scripps Research 2002 - 2010
  • Maimone, Thomas, Ph.D. in Chemistry, Scripps Research 2005 - 2009
  • Richter, Jeremy, Ph.D. in Chemistry, Scripps Research 2003 - 2008

authors

  • Richter, Jeremy
  • Whitefield, B. W.
  • Maimone, Thomas
  • Lin, David Wei
  • Castroviejo, M. P.
  • Baran, Phil

publication date

  • 2007

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Full details are provided for a recently invented method to couple indoles and pyrroles to carbonyl compounds. The reaction is ideally suited for structurally complex substrates and exhibits high levels of chemoselectivity (functional group tolerability), regioselectivity (coupling occurs exclusively at C-3 of indole or C-2 of pyrrole), stereoselectivity (substrate control), and practicality (amenable to scaleup). In addition, quaternary stereocenters are easily and predictably generated. The reaction has been applied to a number of synthetic problems including total syntheses of members of the hapalindole family of natural products, ketorolac, acremoauxin A, and oxazinin 3. Mechanistically, this coupling protocol appears to operate by a single electron-transfer process requiring generation of an electron-deficient radical adjacent to a carbonyl which is then intercepted by an indole or pyrrole anion.

subject areas

  • Carbon
  • Chemistry, Organic
  • Dimerization
  • Electrons
  • Indoles
  • Ketorolac
  • Models, Chemical
  • Molecular Conformation
  • Morpholines
  • Oxazines
  • Oxygen
  • Phosphines
  • Pyrroles
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2631414

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja074392m

PubMed ID

  • 17900115
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Additional Document Info

start page

  • 12857

end page

  • 12869

volume

  • 129

issue

  • 42

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