Synthesis of analogue structures of the p-quinone methide moiety of kendomycin.
[reaction: see text] 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 NaIO(4) on silica produced a long-lived semiquinone radical.
Green
Martin P
MP
Institut für Organische Chemie, Währingerstrasse 38, A-1090 Wien, Austria.
Pichlmair
Stefan
S
Marques
Maria M B
MM
Martin
Harry J
HJ
Diwald
Oliver
O
Berger
Thomas
T
Mulzer
Johann
J
D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry*; D017828:Rifabutin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D007202:Indicators and Reagents; D011809:Quinones; C485395:kendomycin; D017828:Rifabutin