Lithiation chemistry has not been well explored in fluorous synthesis because of the lack of appropriate base-resistant fluorous tags; we recently developed a perfluoroalkylated arylsulfonyl tag for the protection of the indole ring nitrogen atom. Mesityllithium was found to be a suitable reagent for the α-lithiation of perfluoroalkyl-tagged 1-(arylsulfonyl)indole, and the fluorous synthesis of yuehchukene was accomplished efficiently using this method as a key step.
- Fluorous solid-phase extraction
- Fluorous tags
- Indole alkaloids
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry