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Enantioselective Syntheses of FR901464 and Spliceostatin A: Potent Inhibitors of Spliceosome

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journal contribution
posted on 04.10.2013, 00:00 by Arun K. Ghosh, Zhi-Hua Chen
Enantioselective syntheses of FR901464 and spliceostatin A, potent spliceosome inhibitors, are described. The synthesis of FR901464 has been accomplished in a convergent manner in 10 linear steps (20 total steps). The A-tetrahydropyran ring was constructed from (R)-isopropylidene glyceraldehyde. The functionalized tetrahydropyran B-ring was synthesized utilizing a Corey–Bakshi–Shibata reduction, an Achmatowicz reaction, and a stereoselective Michael addition as the key steps. Coupling of A- and B-ring fragments was accomplished via cross-metathesis.