Organic Letters p. 956 - 959 (2010)
Update date:2022-08-05
Topics: Efficient Total synthesis Experimental terms Stereocontrolled (-)-stephanotic acid methyl ester (-)-celogentin C
Hu, Weimin
Zhang, Fengying
Xu, Zhengren
Liu, Qiang
Cui, Yuxin
Jia, Yanxing
(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.
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