Efficient syntheses of rugulosin analogues.
Oxidation of 3b or 14c,d with Pb(OAc)4 in AcOH for 20 min at 25 degrees C and 1 h at 75 degrees C gave flavoskyrin-type dimers 6b and 15c,d in 53-86% yield. Heating a solution of 6b or 15c,d in pyridine under air for 1 h at 75-80 degrees C and then for 1-2 h at 110 degrees C afforded rugulosin-type dimers 10b and 17c,d in 61-88% yield. This two-step sequence provides a practical route to this unusual natural product skeleton.
Snider
Barry B
BB
Department of Chemistry, MS 015, Brandeis University, Waltham, MA 02454-9110, USA. snider@brandeis.edu
Gao
Xiaolei
X
D000880:Anthraquinones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared
D000880:Anthraquinones; C029548:rugulosin