Synthesis of the spiroketal core of integramycin

Abstract

A concise synthetic strategy towards the spiroketal core of the HIV-integrase inhibitor integramycin (1) was developed. The required ketone precursor was efficiently constructed from two simple and easily accessible subunits by means of a hydrozirconation/copper catalyzed acylation reaction. The effects of different protecting groups on the spiroketalization step were also investigated.

Keywords

• anti-infectives
• hydrozirconation
• natural products
• spiroketals
• total synthesis