Co-reporter:Irene De Silvestro;Dr. Samuel L. Drew;Dr. Gary S. Nichol;Dr. Ferna Duarte and;Dr. Andrew L. Lawrence
Angewandte Chemie 2017 Volume 129(Issue 24) pp:6917-6921
Publication Date(Web):2017/06/06
DOI:10.1002/ange.201701481
AbstractThe 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.
Co-reporter:Irene De Silvestro;Dr. Samuel L. Drew;Dr. Gary S. Nichol;Dr. Ferna Duarte and;Dr. Andrew L. Lawrence
Angewandte Chemie International Edition 2017 Volume 56(Issue 24) pp:6813-6817
Publication Date(Web):2017/06/06
DOI:10.1002/anie.201701481
AbstractThe 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.
Co-reporter:Patrick D. Brown
Natural Product Reports (1984-Present) 2017 vol. 34(Issue 10) pp:1193-1202
Publication Date(Web):2017/10/18
DOI:10.1039/C7NP00025A
Covering: up to 2017
This review highlights why careful consideration of the biosynthetic origin (the how) and the biological function (the why) of a natural product can be so useful during the determination of its structure. Recent examples of structural reassignments inspired by biosynthetic and functional insights will be presented. This review will demonstrate the importance of viewing the origin, structure and function of a natural product as intertwined threads of a single story, best viewed as a whole rather than as discrete topics.
Co-reporter:Patrick D. Brown ;Dr. Andrew L. Lawrence
Angewandte Chemie 2016 Volume 128( Issue 29) pp:8561-8565
Publication Date(Web):
DOI:10.1002/ange.201602869
Abstract
Millingtonine is a glycosidic alkaloid that exists as a pair of pseudo-enantiomeric diastereomers. Consideration of the likely biosynthetic origins of this unusual natural product has resulted in the development of a seven-step total synthesis. Results from this synthetic work provide evidence in support of a proposed network of biosynthetic pathways that can account for the formation of several phenylethanoid natural products.
Co-reporter:Patrick D. Brown ;Dr. Andrew L. Lawrence
Angewandte Chemie International Edition 2016 Volume 55( Issue 29) pp:8421-8425
Publication Date(Web):
DOI:10.1002/anie.201602869
Abstract
Millingtonine is a glycosidic alkaloid that exists as a pair of pseudo-enantiomeric diastereomers. Consideration of the likely biosynthetic origins of this unusual natural product has resulted in the development of a seven-step total synthesis. Results from this synthetic work provide evidence in support of a proposed network of biosynthetic pathways that can account for the formation of several phenylethanoid natural products.
Co-reporter:Gonçalo J. L. Bernardes and Andrew L. Lawrence
Chemical Communications 2014 vol. 50(Issue 74) pp:10752-10757
Publication Date(Web):11 Aug 2014
DOI:10.1039/C4CC90250E
A graphical abstract is available for this content
Co-reporter:Gonçalo J. L. Bernardes and Andrew L. Lawrence
Chemical Communications 2014 - vol. 50(Issue 74) pp:NaN10757-10757
Publication Date(Web):2014/08/11
DOI:10.1039/C4CC90250E
A graphical abstract is available for this content
