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- Title
Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative.
- Authors
Dou, Yingchao; Kouklovsky, Cyrille; Gandon, Vincent; Vincent, Guillaume
- 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.
- Subjects
INDOLE alkaloids; ENOL ethers; NATURAL products; INDOLE; BIOSYNTHESIS; SKELETON
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 4, p1543
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201912812