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Synthesis of (-)-neothiobinupharidine

Academic Article
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Overview

related to degree

  • Jansen, Dan, Ph.D. in Chemistry, Scripps Research 2010 - 2015

authors

  • Jansen, Dan
  • Shenvi, Ryan

publication date

  • January 2013

journal

  • Journal of the American Chemical Society  Journal

abstract

  • An eight step, asymmetric synthesis of a dimeric thiaspirane nuphar alkaloid from 3-methyl-2-cyclo-pentenone is reported. The brevity of the route relies on a useful procedure for tandem reductive allylation of cyclopentenones, as well as the minimization of redox manipulations and other functional group interconversions. The distribution of products that arise from spontaneous dimerization points to a more complex biosynthesis.

subject areas

  • Alkaloids
  • Furans
  • Models, Molecular
  • Molecular Conformation
  • Spiro Compounds
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja310778t

PubMed ID

  • 23298203
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Additional Document Info

start page

  • 1209

end page

  • 1212

volume

  • 135

issue

  • 4

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