An efficient and concise total synthesis of the antimalarial alkaloid quindoline

摘要

The preparation of the alkaloid quindoline (1) from indol (3) through a very direct synthetic approach is described in this work. Several successive heteroaromatic lithiation reaction steps were performed in the same medium producing benzylic alcohol (7) in excellent yield. The alcohol was submitted to catalytic reduction, undergoing concomitant cyclization and aromatization, yielding quindoline (1) in 55% overall yield.