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Issue 22, 2013
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Metal triflate-catalyzed cyclization of arylvinylcarbinols: formal synthesis of (±)-dichroanone and (±)-taiwaniaquinone H

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Abstract

A formal synthesis of diterpenoids viz. the taiwaniaquinoids (±)-dichroanone (1a) and (±)-taiwaniaquinone H (1b) possessing an all carbon quaternary stereocenter has been reported. The key step involves a metal triflate-catalyzed cyclization of arylvinylcarbinols, prepared from β-cyclocitral. The reaction possibly follows a stepwise mechanism via the intermediacy of arylallyl carbocationic species.

Graphical abstract: Metal triflate-catalyzed cyclization of arylvinylcarbinols: formal synthesis of (±)-dichroanone and (±)-taiwaniaquinone H

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Publication details

The article was received on 23 Feb 2013, accepted on 04 Apr 2013 and first published on 04 Apr 2013


Article type: Communication
DOI: 10.1039/C3RA41497C
Citation: RSC Adv., 2013,3, 8176-8179
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    Metal triflate-catalyzed cyclization of arylvinylcarbinols: formal synthesis of (±)-dichroanone and (±)-taiwaniaquinone H

    B. N. Kakde, S. De, D. Dey and A. Bisai, RSC Adv., 2013, 3, 8176
    DOI: 10.1039/C3RA41497C

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