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

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Abstract

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.

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

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Supplementary files

Article information


Submitted
23 Apr 2020
Accepted
15 Jun 2020
First published
24 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

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

K. H. (. Park, A. Rizzo and D. Y.-K. Chen, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02299C

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