Bicyclic Ketals: Versatile Intermediates for the Stereocontrolled Construction of Cyclic Ether Derivatives

Hiyoshizo Kotsuki

doi:10.1055/s-1992-21280

Synlett 1992; 1992(2): 97-106
DOI: 10.1055/s-1992-21280

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Bicyclic Ketals: Versatile Intermediates for the Stereocontrolled Construction of Cyclic Ether Derivatives

Hiyoshizo Kotsuki^*

^*Department of Chemistry, Faculty of Science, Kochi University, Akebono-cho, Kochi 780, Japan

Abstract

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The reduction of bicyclic ketal intermediates prepared from readily available chiral ω-ketodiols can serve as a versatile method for the enantioselective construction of cyclic ether derivatives. The reaction proceeds in high stereoselectivity and either cis or trans stereoisomer is accessible by this procedure. The synthetic utility of this method for some natural products containing cyclic ether rings is reviewed. 1. Introduction 2. General Considerations: Bicyclic Ketals 2.1. Preparation of Enantiomerically Pure Bicyclic Ketals 3. Stereoselective Reduction of Bicyclic Ketals 3.1. Stereoselectivity 3.2. Mechanism 3.3. Synthetic Application 3.3.1. Civet Cat Constituent 3.3.2. Isolaurepinnacin Skeleton 3.3.3. Lauthisan 3.4. Stereochemical Prediction by ¹³C NMR Spectroscopy 4. Extension 5. Conclusions

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