A new strategy for the enantiocontrolled synthesis of anthracyclines resulting in a practical route to (+)-4-demethoxydaunomycinone

Abstract

The Diels–Alder reaction of (E)-3-trimethylsilyloxybuta-1,3-dienyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside and 4a,9a-epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetrone is subject to high diastereocontrol; the cycloadduct is converted into (+)-4-demethoxydaunomycinomycinone by a six-step sequence.