Carbon-carbon and carbon-hydrogen bond transformations mediated by highly reactive radicals and their application to the synthesis of bioactive compounds

Takehiko Yoshimitsu, Hiroto Nagaoka, Tetsuaki Tanaka

Research output: Contribution to journalReview article

5 Citations (Scopus)

Abstract

Reactive free radicals have wide applications in organic synthesis due to their remarkable chemical properties that allow useful molecular transformations. The present review covers the author's recent studies on the utilization of radical species in chemical synthesis of organic molecules: The first topic deals with two types of alkoxyl radicals (primary or tertiary) that selectively undergo dehydrogenation or β-scission to give rise to the key structural elements of (-)-CP-263,114, a ras-farnesyl transferase inhibitor. The second part of this review describes the development of new carbon-carbon bond forming reactions that proceed via the direct and selective abstraction of the hydrogen from the sp3C-H bond adjacent to oxygen or nitrogen. In this radical C-H bond transformation, triethylborane serves not only as a source of hydrogen abstractor but as an alkoxyl radical scavenger that enables the irreversible addition of carbon radicals to carbon-oxygen double bonds.

Original languageEnglish
Pages (from-to)665-675
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume65
Issue number7
Publication statusPublished - Jul 1 2007
Externally publishedYes

Keywords

  • (-)-CP-263,114 (Phomoidride B)
  • Alkoxyl radicals
  • C-H hydroxyalkylation
  • C-H transformations
  • Free radicals
  • Hydrogen abstraction
  • Tertiary nitrogen compounds
  • Total synthesis
  • Triethylborane
  • β-amino alcohols
  • β-scission

ASJC Scopus subject areas

  • Organic Chemistry

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