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; Zhen Yang

doi:10.1038/ncomms14233

Nature Communications (Jan 2017)

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,
Zhen Yang

Affiliations

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

DOI: https://doi.org/10.1038/ncomms14233
Journal volume & issue: Vol. 8, no. 1
pp. 1 – 13

Abstract

Read online

Arisandilactone A is a natural product with a complex oxa-bridged tricyclic carbon core, making it a challenging target in total synthesis. Here the authors report an asymmetric total synthesis of its 19-dehydroxy derivative, with homo-Michael and tandem retro-Michael/Michael reactions as key steps.

Published in Nature Communications

ISSN: 2041-1723 (Online)
Publisher: Nature Portfolio
Country of publisher: United Kingdom
LCC subjects: Science
Website: https://www.nature.com/ncomms/

About the journal