Total synthesis of angustine and angustoline. Issue 15 (9th April 2020)

• Record Type: Journal Article
• Authors: Peng, Xin; Fu, Min; Ou, Jingdan; Cao, Ruidi; Song, Hao; Liu, Xiao-Yu; Qin, Yong
• Is Part Of: Tetrahedron letters. Volume 61:Issue 15(2020)
• Publication Date: 2020-04-09
• Subjects: Natural product -- Alkaloid -- Angustine -- Angustoline -- Total synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.151757
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A short total synthesis of the indolopyridine alkaloids angustine (1 ) and angustoline (2 ) has been achieved in five and six steps, respectively. Two key steps for assembly of the pentacyclic core included a Bischler-Napieralski cyclization and a cobalt-catalyzed carbonylative lactamization. A late-stage Mukaiyama hydration allowed the first successful transformation of angustine (1 ) to angustoline (2 ).