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

Org Lett. 2013 Oct 4;15(19):5088-91. doi: 10.1021/ol4024634. Epub 2013 Sep 19.

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Spliceosomes / chemistry
  • Spliceosomes / drug effects*
  • Stereoisomerism

Substances

  • FR 901464
  • Pyrans
  • Spiro Compounds
  • spliceostatin A