Biomimetically inspired asymmetric total synthesis of (+)-19-dehydroxyl arisandilactone A

Yi-Xin Han, Yan-Long Jiang, Yong Li, Hai-Xin Yu, Bing-Qi Tong, Zhe Niu, Shi-Jie Zhou, Song Liu, Yu Lan (), Jia-Hua Chen () and Zhen Yang ()
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Yi-Xin Han: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University
Yan-Long Jiang: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University
Yong Li: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University
Hai-Xin Yu: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University
Bing-Qi Tong: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University
Zhe Niu: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University
Shi-Jie Zhou: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University
Song Liu: School of Chemistry and Chemical Engineering, Chongqing University
Yu Lan: School of Chemistry and Chemical Engineering, Chongqing University
Jia-Hua Chen: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University
Zhen Yang: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University

Nature Communications, 2017, vol. 8, issue 1, 1-13

Abstract: Abstract Complex natural products are a proven and rich source of disease-modulating drugs and of efficient tools for the study of chemical biology and drug discovery. The architectures of complex natural products are generally considered to represent significant barriers to efficient chemical synthesis. Here we describe a concise and efficient asymmetric synthesis of 19-dehydroxyl arisandilactone A—which belongs to a family of architecturally unique, highly oxygenated nortriterpenoids isolated from the medicinal plant Schisandra arisanensis. This synthesis takes place by means of a homo-Michael reaction, a tandem retro-Michael/Michael reaction, and Cu-catalysed intramolecular cyclopropanation as key steps. The proposed mechanisms for the homo-Michael and tandem retro-Michael/Michael reactions are supported by density functional theory (DFT) calculation. The developed chemistry may find application for the synthesis of its other family members of Schisandraceae nortriterpenoids.

Date: 2017
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DOI: 10.1038/ncomms14233

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