Enantioselective Total Synthesis of (+)-Nocardioazine B
The Journal of Organic Chemistry
DOI:10.1021/acs.joc.8b02329
Published:2018-Nov-09(Epub 2018 Nov 09)
Document Type:Journal Article
In this paper, we report an enantioselective total synthesis of (+)-nocardioazine B, a prenylated hexahydropyrrolo[2,3- b]indole (HPI) alkaloid with a central 2,5-diketopiperazine (DKP) ring. The key step in our synthetic route is a copper-catalyzed sequential arylation-alkylation of o-haloanilide derivatives. Based on this transformation, the construction of C3 all-carbon quaternary stereocenters presented in the HPI systems was achieved with high yields and excellent diastereoselectivity.
Addresses:Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology , Yunnan University , Kunming , Yunnan 650091 , P.R. China.
Center for Yunnan-Guizhou Plateau Chemical Functional Materials and Pollution Control , Qujing Normal University , Qujing , Yunnan 655011 , P.R. China.
全文链接：https://pubs.acs.org/doi/10.1021/acs.joc.8b02329
