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Synfacts 2011(3): 0239-0239  
DOI: 10.1055/s-0030-1259410
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of (±)-Maoecrystal V

Contributor(s):Steven V. Ley, James R. Frost
J. 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  
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Publication History

Publication Date:
16 February 2011 (online)

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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.

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