Enantioselective syntheses of FR901464 and spliceostatin A: potent inhibitors of spliceosome.

ABSTRACT: 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.

SUBMITTER: Ghosh AK 

PROVIDER: S-EPMC3827971 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature