Header

UZH-Logo

Maintenance Infos

Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses


Thommen, Christophe; Neuburger, Markus; Gademann, Karl (2016). Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses. Chemistry - A European Journal, 23(1):120-127.

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.

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.

Statistics

Altmetrics

Downloads

0 downloads since deposited on 10 Feb 2017
0 downloads since 12 months

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2016
Deposited On:10 Feb 2017 07:18
Last Modified:10 Aug 2017 13:04
Publisher:Wiley-VCH Verlag
ISSN:0947-6539
Funders:2010 Novartis Early Career Award (to K.G.)
Publisher DOI:https://doi.org/10.1002/chem.201603932

Download

Preview Icon on Download
Content: Published Version
Filetype: PDF - Registered users only
Size: 18MB
View at publisher