Studies towards the total synthesis of spiroquinazoline

Abstract

Presented herein is the synthesis of a key intermediate in the total synthesis of spiroquinazoline. By using N-Boc-serine as starting material, an efficient methodology has been developed to synthesize two types of δ,γ-unsaturated-α-amino acids bearing substitution at either the δ- or γ-position. After this, a novel SN2' reaction which introduces two quaternary centers has been developed. The quinazolinone core of the molecular has been constructed. The progress we made in those key steps paves the way to the first total synthesis of spiroquinazoline.