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Simple reagents for direct halonium-induced polyene cyclizations

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Overview

authors

  • Snyder, Scott
  • Treitler, D. S.
  • Brucks, A. P.

publication date

  • October 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Although there are many reagent combinations that can initiate polyene cyclizations, simple electrophilic halogen sources have not yet proven broadly effective as promoters of such processes. Herein is described a readily prepared and stable class of reagents capable of effecting such transformations for a wide range of electron-rich and -deficient terpenes derived from geraniol, farnesol, and nerol, thereby enabling the effective synthesis of a diverse array of complex chlorine-, bromine-, and iodine-containing polycyclic frameworks. Efforts to date have led to the first racemic laboratory total synthesis and structural revision of the anti-HIV natural product peyssonol A as well as an efficient and concise inaugural total synthesis of peyssonoic acid A. They have also permitted formal racemic total syntheses of aplysin-20, loliolide, K-76, and stemodin to be achieved through routes that are typically shorter, higher-yielding, and more environmentally conscious than previous efforts. Preliminary attempts to use chiral forms of the reagent class for enantioselective alkene halogenation are also described.

subject areas

  • Cyclization
  • Halogens
  • Indicators and Reagents
  • Polyenes
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja106813s

PubMed ID

  • 20858010
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Additional Document Info

start page

  • 14303

end page

  • 14314

volume

  • 132

issue

  • 40

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