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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.[1]

References

  1. Efficient syntheses of rugulosin analogues. Snider, B.B., Gao, X. J. Org. Chem. (2005) [Pubmed]
 
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