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, Vol. 38, No. 1: pp. 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Pharmacy
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1478-6419
• Language: English