Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative. Issue 4 (4th December 2019)

• Record Type: Journal Article
• Authors: Dou, Yingchao; Kouklovsky, Cyrille; Gandon, Vincent; Vincent, Guillaume
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 4(2020)
• Page Start: 1527
• Page End: 1531
• Publication Date: 2019-12-04
• Subjects: cymoside -- furoindoline -- monoterpene indole alkaloids -- oxidative cyclization -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201912812
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The first total synthesis of the caged monoterpene indole alkaloid cymoside is reported. This natural product displays a unique hexacyclic‐fused skeleton whose biosynthesis implies an early oxidative cyclization of strictosidine. Our approach to the furo[3, 2‐ b ]indoline framework relied on an unprecedented biomimetic sequence which started by the diastereoselective oxidation of the indole ring into a hydroxyindolenine which triggered the addition of an enol ether and was followed by the trapping of an oxocarbenium intermediate. Abstract : A bioinspired oxidative cascade cyclization enabled the first total synthesis of cymoside, a monoterpene indole alkaloid which possesses a unique furo[3, 2‐ b ]indoline‐containing hexacyclic‐fused skeleton.