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Total synthesis, assignment of the relative and absolute stereochemistry, and structural reassignment of phostriecin (aka Sultriecin)

Academic Article
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Overview

related to degree

  • Haq, Nadia, Ph.D. in Chemistry, Scripps Research 2002 - 2007

authors

  • Burke, C. P.
  • Haq, Nadia
  • Boger, Dale

publication date

  • February 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A total synthesis of phostriecin (2), previously known as sultriecin (1), its structural reassignment as a phosphate versus sulfate monoester, and the assignment of its relative and absolute stereochemistry are disclosed herein. Key elements of the work, which provided first the originally assigned sulfate monoester 1 and then the reassigned and renamed phosphate monoester 2, relied on diagnostic (1)H NMR spectroscopic properties of the natural product for the assignment of relative and absolute stereochemistry as well as the subsequent structural reassignment, and a convergent asymmetric total synthesis to provide the unequivocal authentic materials. Key steps of the synthetic approach include a Brown allylation for diastereoselective introduction of the C9 stereochemistry, an asymmetric CBS reduction to establish the lactone C5-stereochemistry, diastereoselective oxidative ring expansion of an alpha-hydroxyfuran to access the pyran lactone precursor, and single-step installation of the sensitive Z,Z,E-triene unit through a chelation-controlled cuprate addition with installation of the C11 stereochemistry. The approach allows ready access to analogues that can now be used to probe important structural features required for protein phosphatase 2A inhibition, the mechanism of action defined herein.

subject areas

  • Lactones
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2824046

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja9097252

PubMed ID

  • 20108904
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Additional Document Info

start page

  • 2157

end page

  • 2159

volume

  • 132

issue

  • 7

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