Highly Enantioselective Bromocyclization of Tryptamines and Its Application in the Synthesis of (—)-Chimonanthine

摘要

Cyclotryptamine alkaloids are a family of indole alkaloids encompassing the hexahydropyrrolo[2,3,-b]indole (HPI) ring framework (Figure 1). These alkaloids have been isolated from diverse sources, including bacteria, fungi, higher plants, marine bryozoans, frogs, and human metabolism. It has been proposed that those alkaloids are biologically originated from tryptamine through an oxidative cyclization reaction. A class of cyclotryptamine alkaloids are dimer, trimer, and higher-ordered oligomers of HPI units connected by the C3'-C3 and C3-C7' bonds (chimonanthine and hodgkinsine).