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Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes

Academic Article
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Overview

authors

  • Micalizio, Glenn
  • Roush, William

publication date

  • June 2001

journal

  • Organic Letters  Journal

abstract

  • [see reaction]. A synthesis of tetracycle 2 corresponding to the C(11)-C(26) fragment of pectenotoxin II is described. The synthesis features two highly stereoselective [3 + 2]-annulation reactions of chiral allylsilanes, generated via allylboration of aldehydes with the chiral gamma-silylallylborane 4 or the gamma-silylallylboronate 19, for construction of the highly substituted C and E rings.

subject areas

  • Furans
  • Pyrans
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol0160250

PubMed ID

  • 11405752
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Additional Document Info

start page

  • 1949

end page

  • 1952

volume

  • 3

issue

  • 12

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