Synthesis of Analogue Structures of the
p-Quinone Methide Moiety of
Kendomycin

Green, Martin P.; Pichlmair, Stefan; M. B. Marques, Maria; Martin, Harry J.; Diwald, Oliver; Berger, Thomas; Mulzer, Johann

doi:10.1021/ol048825r.s001

ol048825r_si_001.pdf (378.29 kB)

Synthesis of Analogue Structures of the p-Quinone Methide Moiety of Kendomycin

journal contribution

posted on 2004-09-02, 00:00 authored by Martin P. Green, Stefan Pichlmair, Maria M. B. Marques, Harry J. Martin, Oliver Diwald, Thomas Berger, Johann Mulzer

The synthesis of two model p-quinone methide ring systems of the antibiotic and antiosteoporotic compound kendomycin is reported. Two approaches were examined in detail, and the two-step (i) demethylation and (ii) DMDO oxidation were found to be reliable and generally applicable. Additionally, it was found that oxidation of a benzofuran by NaIO₄ on silica produced a long-lived semiquinone radical.