A short synthesis of (±)-13-deoxyserratine

Abstract : A short and efficient total synthesis of (±)-13-deoxyserratine (3) features a highly stereoselective intramolecular Pauson-Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP = tetrahydropyranyl, TBS = tert-butyldimethylsilyl.