Synthesis of the aglycones of altromycins and kidamycin from a common intermediate

Org Lett. 2005 Aug 18;7(17):3617-20. doi: 10.1021/ol0509742.

Abstract

The aglycone structures 1 and 2, respectively corresponding to the antitumor antibiotic natural products altromycin and kidamycin, have been efficiently synthesized from a common advanced intermediate 3. A series of Claisen condensations and aromatizations affords the anthracene section of 3, followed by annulation of the pyrone ring. The functional groups of 3 can be manipulated for enantioselective introduction of the epoxide side-chain of altromycin aglycone 1, as well as synthesis of the kidamycin aglycone 2. [reaction: see text]

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aminoglycosides / chemical synthesis*
  • Aminoglycosides / chemistry
  • Antibiotics, Antineoplastic / chemical synthesis*
  • Antibiotics, Antineoplastic / chemistry
  • Molecular Structure
  • Streptomyces / chemistry

Substances

  • Aminoglycosides
  • Antibiotics, Antineoplastic
  • kidamycin
  • altromycin A