Modular Bi-Directional One-Pot Strategies for the Diastereoselective Synthesis of Structurally Diverse Collections of Constrained β-Carboline-Benzoxazepines

Vunnam Srinivasulu, Ralph Mazitschek, Noor M. Kariem, Amarnath Reddy, Wael M. Rabeh, Liang Li, Matthew John O'Connor, Taleb H. Al-Tel

Research output: Contribution to journalArticle

Abstract

The development of robust and efficient strategies to access structurally diverse drug-like compound collections remains an important challenge for small molecule probe development and drug discovery. Following a build/couple/pair strategy we have established bidirectional approach to unprecedented benzoxazepines by employing a Pictet–Spengler/aza-Michael addition cascade and Schiff base/aza-Michael addition/reduction protocols, respectively. The corresponding β-carboline-fused benzoxazepines and peripherally substituted benzoxazepines are isolated in high diastereoselectivity, good to excellent yields and have, to the best of our knowledge, never been reported.

Original languageEnglish (US)
Pages (from-to)14182-14192
Number of pages11
JournalChemistry - A European Journal
Volume23
Issue number57
DOIs
StatePublished - Oct 12 2017

Keywords

  • Pictet–Spengler reaction
  • aza-Michael addition
  • benzoxazepines
  • diversity oriented synthesis
  • stereoselective synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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