Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 3, Pages 475-488Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1705953
Keywords
cyclohexane-angularly-fused triquinane; 6-5-5-5 tetra-cycles; natural products; total synthesis; cyclopianes; waihoensene
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Funding
- National Institutes of Health [P01CA025874]
- Petroleum Research Fund
- University of Pennsylvania
- American Chemical Society
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Cyclohexane-angularly-fused triquinanes, 6-5-5-5 tetracycles, have garnered attention from synthetic chemists for their highly congested core structures and multiple quaternary carbon centers. This review focuses on six completed total synthesis of naturally occurring cyclohexane-angularly-fused triquinanes and seven notable methodologies for their synthesis.
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.
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