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Keywords:

  • Natural products;
  • Carbocycles;
  • Cyclopentane;
  • Total synthesis;
  • Asym­metric synthesis;
  • Diels–Alder reaction;
  • Palau'amine

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