CM1407; Alcaloïdes; indole; organométallique; réaction domino; synthèse totale; produit naturel
Torres-Ochoa Rubén O., Buyck Thomas, Wang Qian, Zhu Jieping (2018), Heteroannulation of Arynes with α-Amino Imides: Synthesis of 2,2-Disubstituted Indolin-3-ones and Application to the Enantioselective Total Synthesis of (+)-Hinckdentine A, in Angewandte Chemie International Edition
, 57(20), 5679-5683.
Tong Shuo, Zhao Shun, He Qin, Wang Qian, Wang Mei-Xiang, Zhu Jieping (2017), Fluorophores for Excited-State Intramolecular Proton Transfer by an Yttrium Triflate Catalyzed Reaction of Isocyanides with Thiocarboxylic Acids, in Angew. Chem. Int. Ed
, 56, 6599-6603.
Tong Shuo, Limouni Aurore, Wang Qian, Wang Mei-Xiang, Zhu Jieping (2017), Silver-Catalyzed Three-Component 1,1-Aminoacylation of Homopropargylamines: Dual -Addition between Terminal Alkynes and Isocyanides, in Angew. Chem. Int. Ed
, 56, 14192-14196.
Tong Shuo, Piemontesi Cyril, Wang Qian, Zhu Jieping (2017), Silver-Catalyzed Three-Component 1,1-Aminoacylation of Homopropargylamines: Dual -Addition between Terminal Alkynes and Isocyanides, in Angew. Chem. Int. Ed
, 56, 7958-7962.
Picrinine, first isolated in 1965 by Chatterjee and co-workers, possesses a daunting cage-like polycyclic structure that contains a fused furanoindoline framework, a highly substituted cyclohexane that bears five contiguous stereocenters, a bridged [3.3.1]azabicycle and a bis-hemiaminal function. Picrinine, the main compounds in the total alkaloid extracts, has been proven to be the bioactive constituent responsible for the anti-tussive activity. Alstolactines A-C, isolated in 2014, was biosynthetically derived from picrinine by a sequence of oxidation and lactonization processes.Our proposal deals with the total synthesis of a collection of three structurally complex natural products. The realization of the proposed synthesis would provide us not only an access to these natural products, but also an access to analogues that would help us to better define the structure-activity relationship of this family of bioactive compounds and eventually optimize its structure for the desired biological properties.