5 years ago

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis
Irene De Silvestro, Samuel L. Drew, Gary S. Nichol, Andrew L. Lawrence, Fernanda Duarte
The total synthesis of a dimeric thymol derivative (thymarnicol) isolated from Arnica sachalinensis was accomplished in 6 steps. A key biomimetic Diels–Alder dimerization was found to occur at ambient temperature and the final oxidative cyclization occurs when the substrate is exposed to air and visible light. These results indicate that this natural product is likely the result of spontaneous (non-enzyme-mediated) reactivity. Poised to (re)act: The total synthesis of a dimeric thymol derivative (thymarnicol) isolated from Arnica sachalinensis was accomplished in 6 steps. A key biomimetic Diels–Alder dimerization was found to occur at ambient temperature and the final oxidative cyclization occurs when the substrate is exposed to air and visible light. These results indicate that this natural product is likely the result of spontaneous (non-enzyme-mediated) reactivity.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701481

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