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Synfacts 2007(5): 0451-0451  
DOI: 10.1055/s-2007-968386
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-11-O-Debenzoyltashironin

Contributor(s): Philip Kocienski
S. P. Cook, A. Polara, S. J. Danishefsky*
Columbia University and Sloan-Kettering Institute for Cancer Research, New York, USA
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Publikationsdatum:
24. April 2007 (online)

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Significance

11-O-Debenzoyltashironin, a metabolite of Illicium merrillanium, induces neurite outgrowth in fetal rat cortical neurons. The key step in this biomimetic synthesis is an oxidative dearomatization leading to quinone monoketal B, which underwent an intramolecular Diels-Alder reaction to create all four rings of the target.