Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A. / Jepsen, Tue Heesgaard; Thomas, Stephen; Yunqing, lin; Stathakis, Christos I; Miguel, Irene de; Snyder, Scott A.

In: Angewandte Chemie International Edition, Vol. 53, No. 26, 2014, p. 6747–6751.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Jepsen, TH, Thomas, S, Yunqing, L, Stathakis, CI, Miguel, ID & Snyder, SA 2014, 'Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A', Angewandte Chemie International Edition, vol. 53, no. 26, pp. 6747–6751. https://doi.org/10.1002/anie.201402858

APA

Jepsen, T. H., Thomas, S., Yunqing, L., Stathakis, C. I., Miguel, I. D., & Snyder, S. A. (2014). Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A. Angewandte Chemie International Edition, 53(26), 6747–6751. https://doi.org/10.1002/anie.201402858

Vancouver

Jepsen TH, Thomas S, Yunqing L, Stathakis CI, Miguel ID, Snyder SA. Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A. Angewandte Chemie International Edition. 2014;53(26):6747–6751. https://doi.org/10.1002/anie.201402858

Author

Jepsen, Tue Heesgaard ; Thomas, Stephen ; Yunqing, lin ; Stathakis, Christos I ; Miguel, Irene de ; Snyder, Scott A. / Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A. In: Angewandte Chemie International Edition. 2014 ; Vol. 53, No. 26. pp. 6747–6751.

Bibtex

@article{07a96c040c7b49629a6e1f026a748ca5,
title = "Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A",
abstract = "Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.",
author = "Jepsen, {Tue Heesgaard} and Stephen Thomas and lin Yunqing and Stathakis, {Christos I} and Miguel, {Irene de} and Snyder, {Scott A.}",
year = "2014",
doi = "10.1002/anie.201402858",
language = "English",
volume = "53",
pages = "6747–6751",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH Verlag GmbH & Co. KGaA",
number = "26",

}

RIS

TY - JOUR

T1 - Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A

AU - Jepsen, Tue Heesgaard

AU - Thomas, Stephen

AU - Yunqing, lin

AU - Stathakis, Christos I

AU - Miguel, Irene de

AU - Snyder, Scott A.

PY - 2014

Y1 - 2014

N2 - Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.

AB - Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.

U2 - 10.1002/anie.201402858

DO - 10.1002/anie.201402858

M3 - Journal article

C2 - 24841889

VL - 53

SP - 6747

EP - 6751

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 26

ER -

ID: 124781519