Synthesis and antibiotic activity of the tricyclic furo[3,2-c]isochromen-2-trione unit of the pyranonaphthoquinones.

BIANCHI, DARIO A.; SUTICH, EMMA G.; KAUFMAN, TEODORO S.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Elsevier Science B.V.

Lugar: Amsterdam; Año: 2004 vol. 14 p. 757 - 760

0960-894X

The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig?oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 mg/mL, respectively.