Synfacts 2006(6): 0540-0540  
DOI: 10.1055/s-2006-934493
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Spiruchostatin A

Contributor(s): Philip Kocienski
T. Doi*, Y. Iijima, K. Shin-ya, A. Ganesan, T. Takahashi*
Tokyo Institute of Technology, Japan
Further Information

Publication History

Publication Date:
19 May 2006 (online)

Significance

Spiruchostatin A inhibits histone deacetylases. It has potential for the treatment of cancer. The present synthesis has two notable features: (a) the use of a zirconium enolate to achieve a high diastereomeric ratio in the formation of the β-hydroxy acid C and (b) the penultimate macrolactonization reaction. Spiruchostatin was synthesized previously by S. M. Davidson and co-workers ( ChemBioChem 2005, 6, 162-170).