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Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

Academic Article
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Overview

related to degree

  • Lira, Ricardo, Ph.D. in Chemistry, Scripps Research , Transferred from University of Michigan with advisor 2005 - 2008

authors

  • Nuhant, P.
  • Kister, J.
  • Lira, Ricardo
  • Sorg, A.
  • Roush, William

publication date

  • September 2011

journal

  • Tetrahedron  Journal

abstract

  • Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42 and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% e.e.), diastereoselectivity (d.r. >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.
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Research

keywords

  • Allene hydroboration
  • Double allylboration
  • Kinetically controlled
  • Stereoselective synthesis of syn-1,5-E-diols
  • Studies on the synthesis of tetrafibricin
  • Tetrabutylammonium allenyltrifluoroborate
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Identity

PubMed Central ID

  • PMC3156408

International Standard Serial Number (ISSN)

  • 0040-4020

Digital Object Identifier (DOI)

  • 10.1016/j.tet.2011.06.008

PubMed ID

  • 21857752
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Additional Document Info

start page

  • 6497

end page

  • 6512

volume

  • 67

issue

  • 35

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