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Synthesis 2021; 53(03): 475-488
DOI: 10.1055/s-0040-1705953
DOI: 10.1055/s-0040-1705953
short review
Synthesis of Cyclohexane-Angularly-Fused Triquinanes
We would like to thank the National Institutes of Health (P01-CA025874), the Petroleum Research Fund, administered by the American Chemical Society, and the University of Pennsylvania for financial support.
Dedicated with great affection, admiration and gratitude to Professor Madeleine M. Joullié, who has inspired generations of synthetic chemists with her passion for science, her intellectual rigor and her warmth and humor.
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
Key words
cyclohexane-angularly-fused triquinane - 6-5-5-5 tetracycles - natural products - total synthesis - cyclopianes - waihoensenePublication History
Received: 16 July 2020
Accepted after revision: 24 August 2020
Article published online:
03 November 2020
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For recent isolation of unique naturally occurring polyquinanes, see:
For a review on keteniminium ions, see:
For reviews on metal-catalyzed hydrogen atom transfer strategies, see:
For recent reviews on Lycopodium alkaloids, see:
For the total synthesis of magellanine, see:
For the total synthesis of paniculatine, see:
For the isolation of paniculatine, see:
For similar examples of the synthesis of 6-5-5-5 tetracyclic compounds using the ODPM rearrangement, see:
For recent reviews on the Pauson–Khand reaction, see:
For a review, see: