1. Synthetic study toward the misassigned (±)-tronoharine.
- Author
-
Zhong X, Li Y, Zhang J, and Han FS
- Subjects
- Azepines chemistry, Cyclization, Cycloaddition Reaction, Malaysia, Stereoisomerism, Tabernaemontana chemistry, Indole Alkaloids chemical synthesis, Indole Alkaloids chemistry
- Abstract
The synthesis of a pentacyclic indole compound corresponding to the core structure of the misassigned indole alkaloid, tronoharine (1), is presented. The key reactions were a formal [3 + 3] cycloaddition of an indol-2-yl carbinol with an azadiene for the construction of the 6/5/6/6 tetracyclic system containing an all-carbon quaternary center and an intramolecular substitution reaction of an amine and a triflate for the creation of the bridged azepine ring. In addition, some other interesting transformations discovered during the synthetic studies are also discussed.
- Published
- 2015
- Full Text
- View/download PDF