Enantiodivergent synthesis of either enantiomer of ABCDE-ring analogue of antitumor antibiotic fredericamycin A via intramolecular [4 + 2] cycloaddition approach

Org Lett. 2001 Dec 13;3(25):4015-8. doi: 10.1021/ol016696y.

Abstract

[reaction: see text] An intramolecular enantiodivergent synthesis of both enantiomers of the ABCDE-ring analogue 22 of fredericamycin A is reported. Key steps involve an intramolecular [4 + 2] cycloaddition of 17 and an aromatic Pummerer-type reaction of 19. A lipase-catalyzed enantioselective desymmetrization of prochiral diol 2 using 1-ethoxyvinyl 2-furoate 3 led to the pivotal intermediate (R)-4.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibiotics, Antineoplastic / chemical synthesis
  • Antibiotics, Antineoplastic / chemistry*
  • Candida / enzymology
  • Circular Dichroism
  • Humans
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry*
  • Lipase / metabolism
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Antibiotics, Antineoplastic
  • Isoquinolines
  • Spiro Compounds
  • Lipase
  • fredericamycin A