Total syntheses of carbazole alkaloid mukoenine A and pyrano[3, 2-a]carbazole alkaloid girinimbine. (13th August 2022)

• Record Type: Journal Article
• Authors: Nishiyama, Takashi; Kihara, Yuhto; Takeuchi, Nao; Mizuno, Shota; Hieda, Yuhzo; Hatae, Noriyuki; Choshi, Tominari
• Is Part Of: Tetrahedron. Volume 120(2022)
• Publication Date: 2022-08-13
• Subjects: Mukoenine A -- Grinimbine -- pyrano[3, 2-a]carbazole -- Electrocyclization -- 6π-electron system; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132895
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: In this study, we achieved the total synthesis of carbazole alkaloid mukoenine A through a seven-step sequence involving the construction of a carbazole framework using the electrocyclization of a 6π-electron system including an allene intermediate as the key step. Subsequently, the synthesis of pyrano[3, 2- a ]carbazole alkaloid girinimbine was achieved by the construction of the pyran ring via selenoetherification of the o-allylic phenol moiety of mukoenine A. Graphical abstract: Image 1 Highlights: The total synthesis of mukoenine A has been accomplished via a seven-step sequence. Girinimbine was synthesized by the construction of the pyran ring via mukoenine A. The carbazole framework was constructed by the allene-mediated electrocyclization.