An approach to pancratistatins via ring-closing metathesis: Efficient synthesis of novel 1-aryl-1-deoxyconduritols F

Structurally novel cyclitols, 1-aryl-1-deoxyconduritols F, were efficiently prepared from D-Xylose, utilizing RCM as a key step. Various aromatic residues were incorporated in the cyclitol skeleton with total stereochemical control, utilizing a diestereoselective aryl cuprate addition to a gamma-alkoxy enoate. The synthetic route establishes a firm foundation for a practical synthesis of the antitumor alkaloid pancratistatin and its aryl analogues.