Issue 22, 2013
From the journal:

RSC Advances

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

Badrinath N. Kakde,a   Subhadip De,a   Dhananjay Deya  and  Alakesh Bisai*a  

* Corresponding authors

a Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, M.P.–460 023, India
E-mail: alakesh@iiserb.ac.in

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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Article information

DOI
https://doi.org/10.1039/C3RA41497C
Article type
Communication
Submitted
23 Feb 2013
Accepted
04 Apr 2013
First published
04 Apr 2013

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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