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

✍ Scribed by Ingo V. Hartung; H. Martin R. Hoffmann

Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 533 KB
Volume: 43
Category: Article
ISSN: 0044-8249
DOI: 10.1002/anie.200300622

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✦ Synopsis

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.

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