Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative. (3rd December 2019)

• Record Type: Journal Article
• Authors: Dou, Yingchao; Kouklovsky, Cyrille; Gandon, Vincent; Vincent, Guillaume
• Is Part Of: Angewandte Chemie. Volume 132:Number 4(2020)
• Page Start: 1543
• Page End: 1547
• Publication Date: 2019-12-03
• Subjects: Cymosid -- Furoindolin -- Monoterpen-Indolalkaloide -- Oxidative Cyclisierungen -- Totalsynthese; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201912812
• Languages: English
• ISSNs: 0044-8249

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 : Eine bioinspirierte oxidative Kaskadencyclisierung ermöglichte die erste Totalsynthese von Cymosid, einem Monoterpen‐Indolalkaloid mit einzigartigem, Furo[3, 2‐ b ]indolin‐haltigem, hexacyclischem Gerüst.