Stereocontrolled preparation of fully substituted cyclopentanes: Relevance to total synthesis

Abstract

This Microreview aims to identify important advances in the asymmetric synthesis of fully substituted five-membered carbocyclic ring systems. Recent efforts directed towards the intricate and densely functionalized core substructures of three distinct classes of cydopentane-based natural products will be examined. Strategies featuring high levels of stereocontrol and/or conciseness in the total number of synthetic steps required to access complex natural product ring fragments are highlighted. Stereoselective Diels-Alder cycloaddition approaches to access functionalized norbornene intermediates as latent, chiral cyclopentanes in the tradition of Corey's elegant prostaglandin studies are a recurring theme. © Wiley-VCH Verlag GmbH & Co. KGaA.