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Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses

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)
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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