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Synfacts 2009(5): 0471-0471
DOI: 10.1055/s-0028-1088178
DOI: 10.1055/s-0028-1088178
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Trachyspic Acid
K. Morokuma, Y. Taira, Y. Uehara, S. Shibahara, K. Takahashi, J. Ishihara, S. Hatakeyama*
Nagasaki University, Japan
Further Information
Publication History
Publication Date:
22 April 2009 (online)
Significance
Trachyspic acid is a metabolite of Talaromyces trachyspermus SANK 12191. It has an IC50 value of 36 µM against heparanase, an enzyme that facilitates both tumor invasion and angiogenesis. This asymmetric synthesis utilizes an organocatalytic aldol reaction mediated by thiourea C to introduce the two major stereocenters.