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
