Asymmetric Total Synthesis of Mycoleptodiscin A1. (23rd April 2015)

• Record Type: Journal Article
• Authors: Zhou, Shupeng; Chen, Hao; Luo, Yijie; Zhang, Wenhao; Li, Ang
• Is Part Of: Angewandte Chemie. Volume 127:Number 23(2015)
• Page Start: 6982
• Page End: 6986
• Publication Date: 2015-04-23
• Subjects: Allylische Substitutionen -- C‐N‐Kupplungen -- Indol‐Terpenoide -- Iridium‐Katalyse -- Polyen‐Cyclisierung; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201501021
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The first total synthesis of mycoleptodiscin A, a structurally unusual indolosesquiterpenoid possessing an ortho ‐benzoquinone motif, has been accomplished. A sulfone alkylation coupled two readily available fragments to give an aryl triene intermediate. The tetracyclic core of the molecule was assembled through a highly enantioselective iridium‐catalyzed polyene cyclization. The benzylic homologation was achieved by a cationic cyanation. The indole motif was constructed via a copper‐mediated intramolecular CN bond formation at a late stage.