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Total synthesis of (+/-)-psychotrimine

Academic Article
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Overview

related to degree

  • Newhouse, Timothy, Ph.D. in Chemistry, Scripps Research 2006 - 2010

authors

  • Newhouse, Timothy
  • Baran, Phil

publication date

  • 2008

journal

  • Journal of the American Chemical Society  Journal

abstract

  • new process for the union of anilines with tryptamine derivatives has been developed, furnishing C-3 quaternized pyrroloindoline architectures. This chemoselective coupling of a tryptamine with 1.2 equiv of 2-iodoaniline proceeds efficiently on a gram-scale using only the simple reagents N-iodosuccinimide and triethylamine. Using this new reaction, the complex natural product psychotrimine has been fashioned with a rare level of efficiency and practicality. From a readily available bromotryptamine, only four steps (41-45% overall isolated yield) are necessary to procure gram quantities of the natural product. Functional group manipulations, protecting group chemistry, and unnecessary redox fluctuations have been minimized.

subject areas

  • Indole Alkaloids
  • Molecular Structure
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja8042307

PubMed ID

  • 18656919
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Additional Document Info

start page

  • 10886

end page

  • 10887

volume

  • 130

issue

  • 33

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