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Issue 24, 2009
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An enantiospecific route towards taiwaniaquinoids. First synthesis of (−)-taiwaniaquinone H and (−)-dichroanone

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Abstract

A new methodology for the enantiospecific synthesis of taiwaniaquinoids, based on a thermal 6π electrocyclization, is reported. Under this procedure, 4a-methylhexahydrofluorene terpenoids bearing an A/B trans-configuration has been prepared for the first time. This methodology also makes it feasible to synthesize taiwaniaquinoids with an A/B cis-configuration and 4a-methyltetrahydrofluorene terpenoids. Accordingly, the first synthesis of (−)-taiwaniaquinone G, (−)-taiwaniaquinone H and (−)-dichroanone has been achieved.

Graphical abstract: An enantiospecific route towards taiwaniaquinoids. First synthesis of (−)-taiwaniaquinone H and (−)-dichroanone

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Publication details

The article was received on 07 Aug 2009, accepted on 21 Sep 2009 and first published on 21 Oct 2009


Article type: Paper
DOI: 10.1039/B916209G
Citation: Org. Biomol. Chem., 2009,7, 5146-5155
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    An enantiospecific route towards taiwaniaquinoids. First synthesis of (−)-taiwaniaquinone H and (−)-dichroanone

    E. Alvarez-Manzaneda, R. Chahboun, E. Cabrera, E. Alvarez, A. Haidour, J. M. Ramos, R. Alvarez-Manzaneda, Y. Charrah and H. Es-Samti, Org. Biomol. Chem., 2009, 7, 5146
    DOI: 10.1039/B916209G

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