TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline
Manda Sathish, Akash P. Sakla, Fabiane M. Nachtigall, Leonardo S. Santos, Nagula Shankaraiah
Abstract
-protected tetrahydro-β-carbolines. In this protocol, low equivalents of TCCA were required to access spirooxindoles (up to 99% yield) with a wide substrate scope. Furthermore, the applicability and robustness of this protocol were proven for the gram-scale total synthesis of natural alkaloids such as (±)-coerulescine (1) and (±)-horsfiline (2) in excellent yields.
Topics & Concepts
ChemistryOxidative phosphorylationCombinatorial chemistryBiochemistrySynthesis and bioactivity of alkaloidsChemical synthesis and alkaloidsAsymmetric Synthesis and Catalysis