One-pot high-yielding synthesis of the DPP4-selective inhibitor ABT-341 by a four-component coupling mediated by a diphenylprolinol silyl ether

Hayato Ishikawa, Masakazu Honma, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

94 Citations (Scopus)

Abstract

A dream come true: ABT-341 was synthesized in high yield with excellent diastereo- and enantioselectivity in a one-pot process mediated by a diphenylprolinol silyl ether (see scheme; TMS=trimethylsilyl). Thus, an asymmetric Michael reaction, a domino Michael/Horner-Wadsworth-Emmons reaction combined with a retro-aldol reaction, base-catalyzed isomerization, amide-bond formation, and reduction of the nitro group all took place in a single flask.

Original languageEnglish
Pages (from-to)2824-2827
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number12
DOIs
Publication statusPublished - 2011 Mar 14
Externally publishedYes

Keywords

  • Michael addition
  • asymmetric synthesis
  • domino reactions
  • multicomponent reactions
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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