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Issue 4, 2012
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First enantiospecific synthesis of marine sesquiterpene quinol akaol A

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Abstract

The first enantiospecific synthesis of akaol A, a marine sesquiterpene quinol, has been achieved. Key steps of the synthetic sequence are the oxidative degradation of (−)-sclareol to a dinorlabdane ketoester, mediated by the ozone–lead(IV) acetate system, the diastereoselective α-methylation of a ketoaldehyde, followed by an intramolecular aldol condensation and the further Diels–Alder cycloaddition of a dienol ether.

Graphical abstract: First enantiospecific synthesis of marine sesquiterpene quinol akaol A

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Publication details

The article was received on 27 Jul 2011, accepted on 27 Oct 2011 and first published on 09 Nov 2011


Article type: Communication
DOI: 10.1039/C1CC14608D
Chem. Commun., 2012,48, 606-608

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    First enantiospecific synthesis of marine sesquiterpene quinol akaol A

    E. Alvarez-Manzaneda, R. Chahboun, E. Alvarez, A. Fernández, R. Alvarez-Manzaneda, A. Haidour, J. M. Ramos and A. Akhaouzan, Chem. Commun., 2012, 48, 606
    DOI: 10.1039/C1CC14608D

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