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Synthesis 2011(5): 681-707  
DOI: 10.1055/s-0030-1258335
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Approaches to Enantiomerically Enriched 4-Hydroxycyclohex-2-en-1-one - A Key Chiral Building Block in Complex Natural Product Synthesis

Alan R. Burns, Richard J. K. Taylor*
Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK
Fax: +44(1904)434523; e-Mail: rjkt1@york.ac.uk;
Further Information

Publication History

Received 17 September 2010
Publication Date:
26 November 2010 (online)

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Abstract

4-Hydroxycyclohex-2-en-1-one and its derivatives have been used as the key chiral building blocks in a number of natural product and complex molecule syntheses. This review describes the many and varied methods for preparing the title compound in an enantioselective manner and also details how it has been utilised in natural product synthesis.

1 Introduction

2 Synthetic Methods for Producing Enantiomerically Enriched 4-Hydroxycyclohex-2-en-1-one and Hydroxy-Protected Derivatives

2.1 From the Chiral Pool

2.2 Chiral Auxiliary Approaches

2.3 Desymmetrisation Approaches

2.4 Enantioselective Epoxidation Approaches

2.5 Asymmetric Reduction Approaches

2.6 Asymmetric Deprotonation Approaches

2.7 Kinetic Resolution Approaches

2.8 Organocatalytic α-Aminoxylation Approaches

2.9 Summary of Approaches

3 Applications in Synthesis

3.1 Synthesis of (+)-Compactin

3.2 Synthesis of a Fujimycin (FK-506) Fragment

3.3 Synthesis of (+)-Petasin and (+)-Isopetasin

3.4 Synthesis of 1α,25-Dihydroxy-18-norvitamin D3

3.5 Formal Synthesis of (+)-and (-)-Epibatidine

3.6 Synthesis of (+)-Epiepoformin, (+)-Epiepoxydon and (+)-Bromoxone

3.7 Synthesis of (+)-Apiosporamide and (+)-YM-215343

3.8 Synthesis of (+)-Panepophenanthrin

3.9 Synthesis of (-)-Sordarin

3.10 Synthesis of (+)-Sch 642305

3.11 Synthesis of Kinamycins C, F and J

3.12 Synthesis of (+)-Paeonilactone B

3.13 Synthesis of Otteliones A and B

3.14 Synthesis of (+)-Dictyosphaeric Acid A

3.15 Racemic Syntheses and Miscellaneous Examples

4 Summary

Key words

asymmetric catalysis - chiral auxiliaries - chiral pool - kinetic resolution - natural products