A novel approach to 2-arylmethyl-2,3-dihydro-4(1H)-quinazolinones. Total synthesis of the alkaloids glycozolone-A and glycozolone-B

Klaßmüller, Thomas; Tringali, Claudia und Bracher, Franz (2022): A novel approach to 2-arylmethyl-2,3-dihydro-4(1H)-quinazolinones. Total synthesis of the alkaloids glycozolone-A and glycozolone-B. In: Natural Product Research, Bd. 38, Nr. 1: S. 119-127

Abstract

2-Arylmethyl-2,3-dihydro-4(1H)-quinazolinones are a small subgroup of the class of quinazolin-4-one alkaloids, and most published total syntheses require the use of unstable and poorly accessible arylacetaldehydes. Here we show that easily available, stable omega-methoxystyrenes are versatile substitutes for arylacetaldehydes. This new methodology was applied to the total synthesis of the alkaloids glycozolone-A and glycozolone-B. The limitations of this new approach were analyzed as well. In this course, new total syntheses of two 2-arylmethyl-4(1H)-quinazolinone alkaloids (glycosminine, 2-(4-hydroxybenzyl)-4(1H)-quinazolinone) were developed as well.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department für Pharmazie - Zentrum für Pharmaforschung
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1478-6419
• Sprache: Englisch