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Synthesis of Cyclohexane-Angularly-Fused Triquinanes

Hongjun Jeon, Jeffrey D. Winkler

2020Synthesis23 citationsDOIOpen Access PDF

Abstract

Abstract Cyclohexane-angularly-fused triquinanes, 6-5-5-5 tetra­cycles, have attracted the attention of synthetic chemists due to their highly congested core structures and multiple quaternary carbon centers. This review focuses on the six completed total synthesis of naturally occurring cyclohexane-angularly-fused triquinanes in addition to seven notable methodologies that have been developed for the synthesis of these structures. 1 Introduction 2 6-5-5-5 Tetracycles Containing a Linear Triquinane 2.1 Total Synthesis of Cyclopiane Diterpenes 2.2 Synthetic Approach toward Aberrarane Diterpenes 2.3 Intermediates in the Total Synthesis of Magellanine-Type Alkaloids 3 6-5-5-5 Tetracycles Containing an Angular Triquinane 3.1 Total Synthesis of Waihoensene 3.2 Miscellaneous Approaches 4 Conclusion

Topics & Concepts

CyclohexaneChemistryQuaternary carbonOrganic chemistryCatalysisEnantioselective synthesisSynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisCatalytic Cross-Coupling Reactions