Enabling syntheses of diterpenoid alkaloids and related diterpenes by an oxidative dearomatization/Diels-Alder cycloaddition strategy

Covering: 2015 to March 2017 ortho -Benzoquinones generated from dearomatization of aromatic compounds are highly reactive intermediates in organic synthesis. One of their most important applications involves the participation in Diels-Alder cycloadditions, facilitating rapid access to molecular com...

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Published inNatural product reports Vol. 34; no. 9; pp. 144 - 15
Main Authors Liu, Xiao-Yu, Qin, Yong
Format Journal Article
LanguageEnglish
Published England 30.08.2017
Subjects
Alkaloids - chemical synthesis
Alkaloids - chemistry
benzoquinones
Cycloaddition Reaction
cycloaddition reactions
Diterpenes - chemical synthesis
Diterpenes - chemistry
diterpenoid alkaloids
Molecular Structure
Oxidation-Reduction
Stereoisomerism
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Summary:Covering: 2015 to March 2017 ortho -Benzoquinones generated from dearomatization of aromatic compounds are highly reactive intermediates in organic synthesis. One of their most important applications involves the participation in Diels-Alder cycloadditions, facilitating rapid access to molecular complexity. This powerful strategy has recently been utilized in the syntheses of diverse diterpenoid alkaloids and their biogenetically relevant diterpenes, which is the subject of this Highlight. Recent accomplishments in the total syntheses of diterpenoid alkaloids and their biosynthetically associated diterpenes have highly relied on an oxidative dearomatization/Diels-Alder cycloaddition strategy, and are highlighted in this article.
Bibliography:Yong Qin received his BS degree from Yunnan University in 1989 and his PhD from the Institute of Chemistry, Chinese Academy of Sciences in 1995. After a short stay at the Chengdu Institute of Organic Chemistry as an assistant and associate professor, he moved to the USA, working as a postdoctoral associate (1996 to 2000) at the University of Vermont. He was a research scientist at Triad Therapeutics (San Diego) before he joined the faculty of Sichuan University as a full professor in 2003. His research has been focused on the total synthesis of bioactive natural products and medicinal chemistry.
Xiao-Yu Liu was born in 1985 in Sichuan Province, China. He received his PhD degree in 2012 under the supervision of Prof. Feng-Peng Wang at Sichuan University. He then carried out postdoctoral studies at Seoul National University with Prof. David Y.-K. Chen. After that, he joined the faculty of Sichuan University in 2014 working with Prof. Yong Qin. His research interests include target- and diversity-oriented synthesis based on complex natural products, especially the diterpenoid alkaloids.
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ISSN:0265-0568
1460-4752
1460-4752
DOI:10.1039/c7np00033b