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8‐Oxabicyclo[3.2.1]oct‐6‐en‐3‐ones: Application to the Asymmetric Synthesis of Polyoxygenated Building Blocks

2004; Wiley; Volume: 43; Issue: 15 Linguagem: Inglês

10.1002/anie.200300622

1521-3773

Ingo V. Hartung, H. M. R. Hoffmann,

Chemical synthesis and alkaloids

Abstract The development and design of reliable and efficient methods for the construction of chiral building blocks are crucial in modern natural product synthesis. 8‐Oxabicyclo[3.2.1]oct‐6‐en‐3‐ones are readily accessible scaffolds with defined stereochemical features which have been exploited for non‐aldol approaches to the preparation of chiral building blocks. Strategies for their enantioselective synthesis, including asymmetric cycloaddition methods, desymmetrization protocols, and “racemic switch operations”, are presented and evaluated.