Traceless solid-phase synthesis of mappicine ketone library via multiple chemoselective palladium-catalyzed reactions on benzenesulfonate linker

Hirokazu Tsukamoto, Risako Suzuki, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

We report here a solid-phase synthesis of a library of mappicine ketone, a leading antiviral compound with activity against herpes viruses and human cytomegalovirus. The synthesis is based on multiple chemoselective palladium-catalyzed reactions involving a regioselective intramolecular Heck reaction at C-2, substitution of Cl at C-7 by Suzuki-Miyaura cross-coupling reaction and Buchwald-Hartwig amination, and reductive cleavage of the benzenesulfonate linker at C-1O.

Original languageEnglish
Pages (from-to)2005-2010
Number of pages6
JournalSynlett
Issue number13
DOIs
Publication statusPublished - 2008 Aug 1

Keywords

  • Benzenesulfonate linker
  • Chemoselective
  • Mappicine ketone
  • Palladium
  • Traceless solid-phase synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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