Synthesis of (+)-Trachyspic Acid

K. Morokuma; Y. Taira; Y. Uehara; S. Shibahara; K. Takahashi; J. Ishihara; S. Hatakeyama

doi:10.1055/s-0028-1088178

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Synfacts 2009(5): 0471-0471
DOI: 10.1055/s-0028-1088178

Synthesis of Natural Products and Potential Drugs

Synthesis of (+)-Trachyspic Acid

Contributor(s): Philip Kocienski, Stewart Eccles
K. Morokuma, Y. Taira, Y. Uehara, S. Shibahara, K. Takahashi, J. Ishihara, S. Hatakeyama*
Nagasaki University, Japan

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Publication History

Publication Date:
22 April 2009 (online)

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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.