Abstract

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 ( £ )-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.

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