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Paper | Special issue | Vol 76, No. 1, 2008, pp.275-290
Published online, 11th March, 2008
DOI: 10.3987/COM-07-S(N)5
Total Synthesis of Spiruchostatin A — A Potent Histone Deacetylase Inhibitor

Toshiya Takizawa, Kazuhiro Watanabe, Koichi Narita, Kyosuke Kudo, Takamasa Oguchi, Hideki Abe, and Tadashi Katoh*

*Laboratory of Medicinal Synthetic Chemistry, Department of Chemical Pharmaceutical Science, Tohoku Pharmaceutical University, Komatsushima, Aoba-ku, Sendai 981-8558, Japan


Total synthesis of spiruchostatin A (1), a potent histone deacetylase inhibitor, was achieved; the method features (i) Julia-Kocienski olefination of sulfone 10 and aldehyde 11 to install the requisite (E)-olefin unit present in segment 6, (ii) amide coupling of segment 5 with segment 6 to produce the key seco-acid 4, and (iii) macrolactonization of 4 employing Shiina reagent to efficiently construct the desired 15-membered macrocyclic compound 32.