Late-stage and strain-accelerated oxidation enabled synthesis of haouamine A

Herein we report a new synthetic entry to the strained cyclophane alkaloid natural product, haouamine A. The successful strategy featured a rhodium-catalyzed diazo-insertion reaction to install the all-carbon quaternary center and a rhodium-catalyzed intramolecular aziridination reaction to establis...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-08, Vol.11 (31), p.8132-8137
Main Authors: Park, Kun Ho (Kenny), Rizzo, Antonio, Chen, David Y.-K
Format: Article
Language:English
Subjects:
Catalysis
Deoxygenation
Natural products
Oxidation
Rhodium
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Summary:Herein we report a new synthetic entry to the strained cyclophane alkaloid natural product, haouamine A. The successful strategy featured a rhodium-catalyzed diazo-insertion reaction to install the all-carbon quaternary center and a rhodium-catalyzed intramolecular aziridination reaction to establish the nitrogen-bearing stereocenter, of the target molecule. Most notably, a late-stage, site-selective and strain-accelerated oxidation of a "deoxygenated" macrocyclic intermediate was successfully implemented, and in doing so provided a novel solution to the infamous biphenol cyclophane system of haouamine A. Synthesis of the strained cyclophane alkaloid haouamine A has been accomplished via a late-stage and strain-accelerated oxidation to access the challenging biphenol cyclophane system.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc02299c