Synthesis and application of 1,2-aminoalcohols with neoisopulegol-based octahydrobenzofuran core

Fatima Zahra Bamou, Tam Minh Le, Bettina Volford, András Szekeres, Z. Szakonyi

Research output: Contribution to journalArticle

Abstract

A library of 1,2-aminoalcohol derivatives with a neoisopulegol-based octahydrobenzofuran core was developed and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The allylic chlorination of (+)-neoisopulegol, derived from natural (-)-isopulegol followed by cyclization, gave the key methyleneoctahydrobenzofuran intermediate. The stereoselective epoxidation of the key intermediate and subsequent oxirane ring opening with primary amines afforded the required 1,2-aminoalcohols. The ring closure of the secondary amine analogues with formaldehyde provided spiro-oxazolidine ring systems. The dihydroxylation of the methylenetetrahydrofuran moiety with OsO4/NMO (4-methylmorpholine N-oxide) resulted in the formation of a neoisopulegol-based diol in a highly stereoselective reaction. The antimicrobial activity of both the aminoalcohol derivatives and the diol was also explored.

Original languageEnglish
Article number21
JournalMolecules
Volume25
Issue number1
DOIs
Publication statusPublished - 2020

Keywords

  • 1 2-aminoalcohol
  • Antimicrobial activity
  • Chiral catalyst
  • Neoisopulegol
  • Octahydrobenzofuran

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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