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Synfacts 2009(1): 0003-0003
DOI: 10.1055/s-0028-1087237
DOI: 10.1055/s-0028-1087237
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Rubioncolin B
Contributor(s):Philip KocienskiJ.-P. Lumb, K. C. Choong, D. Trauner*
University of California at Berkeley, USA
ortho-Quinone Methides from para-Quinones: Total Synthesis of Rubioncolin B
J. Am. Chem. Soc. 2008, 130: 9230-9231
University of California at Berkeley, USA
ortho-Quinone Methides from para-Quinones: Total Synthesis of Rubioncolin B
J. Am. Chem. Soc. 2008, 130: 9230-9231
Further Information
Publication History
Publication Date:
18 December 2008 (online)
Key words
rubioncolin B - quinone methide - Diels-Alder reaction
Significance
Rubioncolin B is isolated from the roots of Rubia species which are administered in Chinese medicine. The short synthesis depicted features the tautomerization of the p-quinone I to the o-quinone methide J which then undergoes an intramolecular Diels-Alder reaction to give the complex ring system of the target.
Comment
Natural rubioncolin B is racemic and the authors postulate that the tautomerization of p-quinone I to the o-quinone methide J and a subsequent Diels-Alder reaction may explain its biogenesis.