Stereocontrolled Preparation of Fully Substituted Cyclopentanes: Relevance to Total Synthesis

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 cyclopentane-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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)