A new route toward 4-substituted pyrazino[2,1-b]quinazoline-3,6-dione systems. Total synthesis of glyantrypine

J Org Chem. 2000 Mar 24;65(6):1743-9. doi: 10.1021/jo991626e.

Abstract

Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Resistance, Multiple
  • Magnetic Resonance Spectroscopy
  • Quinazolines / chemical synthesis*
  • Stereoisomerism
  • Tryptophan / analogs & derivatives*
  • Tryptophan / chemical synthesis

Substances

  • Quinazolines
  • glyantrypine
  • Tryptophan