Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Irene DeSilvestro; Samuel Drew; Gary S. Nichol; Fernanda  Duarte; Andrew Lawrence

doi:10.1002/anie.201701481

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Irene DeSilvestro, Samuel Drew, Gary S. Nichol, Fernanda Duarte, Andrew Lawrence

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
Pages (from-to)	6813-6817
Journal	Angewandte Chemie International Edition
Volume	56
Issue number	24
DOIs	https://doi.org/10.1002/anie.201701481
Publication status	Published - 2017

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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",

author = "Irene DeSilvestro and Samuel Drew and Nichol, {Gary S.} and Fernanda Duarte and Andrew Lawrence",

year = "2017",

doi = "10.1002/anie.201701481",

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volume = "56",

pages = "6813--6817",

journal = "Angewandte Chemie International Edition",

publisher = "Wiley-VCH Verlag GmbH",

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AU - DeSilvestro, Irene

AU - Drew, Samuel

AU - Nichol, Gary S.

AU - Duarte, Fernanda

AU - Lawrence, Andrew

PY - 2017

Y1 - 2017

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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

U2 - 10.1002/anie.201701481

DO - 10.1002/anie.201701481

M3 - Article

VL - 56

SP - 6813

EP - 6817

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 24

ER -

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Abstract

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