Thommen, Christophe and Neuburger, Markus and Gademann, Karl. (2017) Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses. Chemistry - A European Journal, 23 (1). pp. 120-127.
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Official URL: http://edoc.unibas.ch/59103/
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Abstract
A divergent synthesis of 10 icetexane natural products based on a proposed biogenetic cationic ring expansion of a reduced carnosic acid derivative is described. Of these icetexanes, (+)-salvicanol, (−)-cyclocoulterone, (−)-coulterone, (−)-obtusinone D, and (−)-obtusinone E have been synthesized for the first time. In addition, the hypothesis for the non-enzymatic biogenesis of benzo[1,3]dioxole natural products has been experimentally investigated. Additional experimental evidence for the abiotic formation of the methylenedioxy unit is provided, as photolysis of the quinone (+)-komaroviquinone resulted in the formation of the [1,3]dioxole-containing natural product (−)-cyclocoulterone and (+)-komarovispirone.
Faculties and Departments: | 05 Faculty of Science > Departement Chemie 05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Chemie (Gademann) |
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UniBasel Contributors: | Thommen, Christophe and Neuburger, Markus and Gademann, Karl |
Item Type: | Article, refereed |
Article Subtype: | Research Article |
Publisher: | Wiley |
ISSN: | 0947-6539 |
e-ISSN: | 1521-3765 |
Note: | Publication type according to Uni Basel Research Database: Journal article |
Identification Number: | |
Last Modified: | 24 Jan 2018 11:18 |
Deposited On: | 24 Jan 2018 11:13 |
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