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Synfacts 2006(5): 0415-0415  
DOI: 10.1055/s-2006-934397
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Microphyllaquinone

Contributor(s): Philip Kocienski, Thomas Snaddon
J.-P. Lumb, D. Trauner*
University of California at Berkeley, USA
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

Extracts of the roots from Lippia microphylla have long been used in Brazilian traditional medicine as expectorants, astringents and diuretics. Naphthoquinone dimer microphylla­quinone has recently been identified as one of the active components and it displays cytotoxic activity. Noteworthy in this synthesis is (1) the conjugate addition of functionalized organocopper ­reagent E to D and (2) the biomimetic oxa 6π-electrocyclization of putative ortho-quinone methide H to form the central pyran ring.