Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative |
| |
Authors: | Yingchao Dou Cyrille Kouklovsky Vincent Gandon Guillaume Vincent |
| |
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 furo3,2‐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. |
| |
Keywords: | cymoside furoindoline monoterpene indole alkaloids oxidative cyclization total synthesis |
|