Total synthesis of atropurpuran

Jing Gong, Huan Chen, Xiao-Yu Liu, Zhi-Xiu Wang, Wei Nie and Yong Qin ()
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Jing Gong: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China
Huan Chen: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China
Xiao-Yu Liu: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China
Zhi-Xiu Wang: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China
Wei Nie: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China
Yong Qin: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China

Nature Communications, 2016, vol. 7, issue 1, 1-6

Abstract: Abstract Due to their architectural intricacy and biological significance, the synthesis of polycyclic diterpenes and their biogenetically related alkaloids have been the subject of considerable interest over the last few decades, with progress including the impressive synthesis of several elusive targets. Despite tremendous efforts, conquering the unique structural types of this large natural product family remains a long-term challenge. The arcutane diterpenes and related alkaloids, bearing a congested tetracyclo[5.3.3.04,9.04,12]tridecane unit, are included in these unsolved enigmas. Here we report a concise approach to the construction of the core structure of these molecules and the first total synthesis of (±)-atropurpuran. Pivotal features of the synthesis include an oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade, sequential aldol and ketyl-olefin cyclizations to assemble the highly caged framework, and a chemoselective and stereoselective reduction to install the requisite allylic hydroxyl group in the target molecule.

Date: 2016
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DOI: 10.1038/ncomms12183

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