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Synfacts 2011(3): 0239-0239
DOI: 10.1055/s-0030-1259410
DOI: 10.1055/s-0030-1259410
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Total Synthesis of (±)-Maoecrystal V
Rezensent(en):Steven V. Ley, James R. FrostJ. Gong, G. Lin, W. Sun, C.-C. Li*, Z. Yang*
Peking University, Beijing and Shenzen Graduate School of Peking University, P. R. of China
Total Synthesis of (±)-Maoecrystal V
J. Am. Chem. Soc. 2010, 132: 16745-16746
Peking University, Beijing and Shenzen Graduate School of Peking University, P. R. of China
Total Synthesis of (±)-Maoecrystal V
J. Am. Chem. Soc. 2010, 132: 16745-16746
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
16. Februar 2011 (online)
Key words
Wessely oxidative acetoxylation - intramolecular Diels-Alder reaction - rhodium-catalyzed O-H insertion
Significance
Maoecrystal V was isolated in 2004 by Sun from the Chinese herb Isodon eriocalyx. Both the congested framework and biological inhibition against HeLa cells (IC50 = 60 nm) has made maoecrystal V a worthy target for the synthetic community.
Comment
Key steps involve the formation of the seven-membered ring via a rhodium-catalyzed O-H insertion to give H. The pentacyclic system was completed by use of a Wessely oxidative acetoxylation followed by an intramolecular Diels-Alder reaction in which L was the major product.