Total Synthesis of (-)-Conolutinine

Feng X 1 , Jiang G 2 , Xia Z 2 , Hu J 1 , Wan X 3 , Gao JM 1 Show all authors , Lai Y 2 , Xie W 1

Affiliations 

  • 1 Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , 22 Xinong Road, Yangling 712100, Shaanxi, China
  • 2 State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, Center of Drug Discovery, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China
  • 3 State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China
Org. Lett., 2015 Sep 18;17(18):4428-31.
PMID: 26315849 DOI: 10.1021/acs.orglett.5b02046

Abstract

The first enantioselective synthesis of (-)-conolutinine was achieved in 10 steps. The synthesis featured a catalytic asymmetric bromocyclization of tryptamine to forge the tricycle intermediate. Hydration of an alkene catalyzed by Co(acac)2 was also employed as a key step to diastereoselectively introduce the tertiary alcohol moiety. The absolute configuration of (-)-conolutinine was established to be (2S,5aS,8aS,13aR) based on this asymmetric total synthesis.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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