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Synfacts 2009(8): 0925-0925  
DOI: 10.1055/s-0029-1217499
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

A Solid-Phase Total Synthesis of Spiruchostatin A

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
Y. Iijima, A. Munakata, K. Shin-ya, A. Ganesan, T. Doi*, T. Takahashi*
Tokyo Institute of Technology, Japan Biological Informatics Consortium, Tokyo, National Institute of Advanced Industrial Science and Technology, Tokyo, Tohoku University, Sendai, Japan and University of Southampton, UK
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

A solid-phase total synthesis of spiruchostatin A (9) was described. Thus, the linear peptide 7 was prepared by the standard Fmoc method using a 2-chlorotrityl resin support. The polymer support was cleaved by treatment of 7 (W = polymer support) with hexafluoroisopropyl alcohol to give the linear peptide 8 (W = OH). The macrolactonization of 8 with Shina’s method followed by disulfide bond formation afforded spiruchostatin A in 89% yield.