Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses

详细信息    查看全文

• 作者：Dr. Christophe Thommen ; Dr. Markus Neuburger and Prof. Dr. Karl Gademann
• 刊名：Chemistry - A European Journal
• 出版年：2017
• 出版时间：January 1, 2017
• 年：2017
• 卷：23
• 期：1
• 页码：120-127
• 全文大小：1560K
• ISSN：1521-3765

文摘

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.