Asymmetric approach towards the total synthesis of (+)-actinopyllic acid. Issue 15 (13th April 2017)

• Record Type: Journal Article
• Authors: Xue, Fei; Xiao, Tao; Li, Min; Zhang, Kai-Fang; He, Li-Ping; Qin, Yong; Liu, Xiao-Yu; Zhang, Dan
• Is Part Of: Tetrahedron. Volume 73:Issue 15(2017)
• Page Start: 2109
• Page End: 2115
• Publication Date: 2017-04-13
• Subjects: Actinopyllic acid -- Asymmetric synthesis -- Indole synthesis -- Chiral oxazolidinone -- Alstonia actinophylla; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.02.058
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: This paper describes our efforts towards the asymmetric total synthesis of (+)-actinophyllic acid. Starting from the chiral oxazolidinone9, an azocino [4, 3- b ]indolyl intermediate (5 ) possessing the A/B/C ring system and the C16 quaternary stereogenic center of actinophyllic acid has been synthesized. Key steps include a LHMDS-promoted condensation to establish the critical C2–C16 bond and a successive four-step transformation to assemble the eight-membered C-ring of the target molecule. Graphical abstract: