Synthetic studies of cyclic peptides stephanotic acid methyl ester, celogentin C, and moroidin
An account of the total synthesis of stephanotic acid methyl ester and celogentin C is presented. The present synthesis features a tandem asymmetric Michael addition/bromination sequence for the synthesis of leucine-tryptophan moiety, and an oxidative coupling reaction to form the tryptophan-imidazole linkage. Moreover, the total synthesis of moroidin had also been studied, and three different synthetic strategies for the construction of the right-hand ring of moroidin were studied.
Li, Lei,Hu, Weimin,Jia, Yanxing
p. 7753 - 7762
(2014/12/10)
Stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C
(Figure Presented) A highly stereocontrolled and efficient total synthesis of (-)-stephanotlc acid methyl ester and (-)-celogentin C was accomplished In longest linear 14 steps (4.6% overall yield) and In 20 steps (1.6% overall yield) from L-tryptophan, respectively. Highlights of the synthesis include a tandem asymmetric Michael addition/bromination/azidation strategy for a ready access to the leucine-tryptophan moiety (Leu-Trp linkage) and an oxidative coupling reaction to form the indole-imidazole linkage.