Total Synthesis of Hypersampsone M
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1.
California Institute of Technology
Abstract
We report the first total synthesis of hypersampsone M, an archetypal member of the homoadamantane polycyclic polyprenylated acylphloroglucinols (PPAPs). Commencing from cyclohexenone, a key cyclopentene annulation followed by ring-expansion results in an elusive hydrazulene that undergoes a series of unexpected late-stage transformations, ultimately enabling completion of the synthesis. The route detailed herein represents a potentially general strategy for the synthesis of related homoadamantane PPAPs.
Copyright and License
© 2024 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY-NC-ND 4.0.
Acknowledgement
The NIH-NIGMS (R35GM145239), Heritage Medical Research Investigators Program, and Caltech, are thanked for their support of our research program. Preparative HPLC was performed with instrumentation at the Caltech Center for Catalysis and Chemical Synthesis, a facility of the Beckman Institute at Caltech. We thank Dr. David VanderVelde (Caltech) for NMR expertise and Dr. Mona Shagholi (Caltech) for mass spectrometry assistance. We graciously thank Kasam Poonswat, Hanh T. Nguyen, and Kevin J. Gonzalez for many helpful discussions. A.E.S. would like to thank Prof. Robert H. Grubbs for his support, and the NSF GRFP for funding.
Data Availability
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Experimental procedures, spectroscopic data (1H NMR, 13C NMR, IR, and HRMS) (PDF)
Conflict of Interest
The authors declare no competing financial interest.
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Additional details
- ISSN
- 1520-5126
- National Institutes of Health
- R35GM145239
- California Institute of Technology
- Heritage Medical Research Institute
- National Science Foundation
- NSF Graduate Research Fellowship
- Caltech groups
- Heritage Medical Research Institute