Total Synthesis of Hypersampsone M

Total Synthesis of Hypersampsone M

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 146; no. 28; pp. 18886 - 18891
Main Authors: Samkian, Adrian E., Virgil, Scott C., Stoltz, Brian M.
Format: Journal Article
Language:English
Published: United States American Chemical Society 17-07-2024
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Summary: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.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.4c07007