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Stereocontrolled and Efficient Total Synthesis of (−)-Stephanotic Acid Methyl Ester and (−)-Celogentin C

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journal contribution
posted on 05.03.2010, 00:00 by Weimin Hu, Fengying Zhang, Zhengren Xu, Qiang Liu, Yuxin Cui, Yanxing Jia
A highly stereocontrolled and efficient total synthesis of (−)-stephanotic 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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