Efficient Syntheses of Rugulosin Analogues
- 26 July 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (17) , 6863-6869
- https://doi.org/10.1021/jo0508898
Abstract
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.Keywords
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