Construction of spirolactones with concomitant formation of the fused quaternary centre – application to the synthesis of natural products

Abstract

Covering: up to the end of 2010

Polycyclic structures fused at a central carbon are of great interest due to their appealing conformational features and their structural implications in biological systems. Although progress in the development of synthetic methodologies towards such structures has been impressive, the stereoselective construction of such quaternary stereocentres remains a significant challenge in the total synthesis of natural products. This review highlights the progress in the formation of 1-oxaspiro[4.n]alkan-2-ones (2 ≤ n ≤ 7) with concomitant formation of the quaternary spiro centre.