Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Samuel L. Drew; Fernanda Duarte Gonzalez; Irene De silvestro; Andrew Lawrence; Gary Nichol

doi:10.1002/ange.201701481

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Samuel L. Drew, Fernanda Duarte Gonzalez, Irene De silvestro, Andrew Lawrence, Gary Nichol

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Journal	Angewandte Chemie
Early online date	5 May 2017
DOIs	https://doi.org/10.1002/ange.201701481
Publication status	Published - 5 May 2017

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10.1002/ange.201701481

20170503 Lawrence_ACIE_Manuscript_ThymarnicolAccepted author manuscript, 525 KBLicence: Creative Commons: Attribution Non-Commercial (CC-BY-NC)

http://doi.wiley.com/10.1002/ange.201701481

Andrew Lawrence
- a.lawrenceed.acuk
- School of Chemistry - Personal Chair of Organic Synthesis
- EaStCHEM
Person: Academic: Research Active

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title = "Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis",

abstract = "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.",

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AU - De silvestro, Irene

AU - Lawrence, Andrew

AU - Nichol, Gary

PY - 2017/5/5

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AB - 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.

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DO - 10.1002/ange.201701481

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SN - 0044-8249

JO - Angewandte Chemie

JF - Angewandte Chemie

ER -

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Abstract

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Andrew Lawrence

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