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Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane

Academic Article
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Overview

authors

  • Tinsley, J. M.
  • Mertz, E.
  • Chong, P. Y.
  • Rarig, R. A. F.
  • Roush, William

publication date

  • September 2005

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] A total synthesis of (+)-bullatacin has been accomplished via a diastereoselective [3+2] annulation reaction of the highly enantiomerically enriched allylsilane 3 and racemic aldehyde 4, which provides the key bis-tetrahydrofuran fragment 15 with > or = 20:1 ds.

subject areas

  • Aldehydes
  • Alkenes
  • Boron
  • Furans
  • Hydroxylation
  • Kinetics
  • Molecular Structure
  • Silanes
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2507730

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol051719k

PubMed ID

  • 16146398
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Additional Document Info

start page

  • 4245

end page

  • 4248

volume

  • 7

issue

  • 19

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