期刊
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
卷 95, 期 6, 页码 871-881出版社
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20220049
关键词
Alkaloids; Asymmetric synthesis; Total synthesis
资金
- JSPS KAKENHI [JP17H05051, JP21H02131]
- Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED [JP19am0101092j0003]
In this study, we successfully synthesized the core structure of Lyconesidine B and achieved stereoselective derivatization using different synthetic strategies. The synthesis of the tetracyclic core structure was achieved through cyclopropanation and ene-yne metathesis, while the asymmetric cyclopropanation introduced the initial chiral center.
Lyconesidine B, isolated from Lycopodium chinense, is characterized by an oxygenated amine core and a trans-fused CD ring with a hydroxymethyl group on the axial position. Because the oxidation level of C13 of this alkaloid is different from other fawcettimine-type alkaloids, we investigated a suitable strategy for its synthesis. As a result, we established a synthetic route to the CD ring decahydroquinoline via cyclopropanation followed by ring-opening and reduction, and the AB ring tetracyclic core by ene-yne metathesis. In the ene-yne metathesis, the use of a quatemary ammonium salt solved the issues of the conformation of the substrate as well as the deactivation of the catalyst. The first total synthesis was achieved by stereoselective derivatization of the tetracyclic skeleton. In addition, we investigated the asymmetric cyclopropanation, which introduces an initial chiral center and was found to be effective for a Ru catalyst with vinyloxazoline-type ligands.
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