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Issue 19, 2005
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A new and efficient method for o-quinone methide intermediate generation: application to the biomimetic synthesis of the benzopyran derived natural products (±)-lucidene and (±)-alboatrin

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Abstract

Lucidene and alboatrin are complex benzopyran derived natural products. A key step in their biogenesis may involve a hetero Diels–Alder cycloaddition between an o-quinone methide intermediate with a simple, or activated tri-substituted olefin. Experimental evidence is provided to support this hypothesis, with the biomimetic synthesis of both (±)-lucidene and (±)-alboatrin successfully achieved using a new and efficient method for o-quinone methide generation.

Graphical abstract: A new and efficient method for o-quinone methide intermediate generation: application to the biomimetic synthesis of the benzopyran derived natural products (±)-lucidene and (±)-alboatrin

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Supplementary files

Article information


Submitted
28 Jun 2005
Accepted
25 Jul 2005
First published
07 Sep 2005

Org. Biomol. Chem., 2005,3, 3488-3495
Article type
Paper

A new and efficient method for o-quinone methide intermediate generation: application to the biomimetic synthesis of the benzopyran derived natural products (±)-lucidene and (±)-alboatrin

R. Rodriguez, J. E. Moses, R. M. Adlington and J. E. Baldwin, Org. Biomol. Chem., 2005, 3, 3488
DOI: 10.1039/B508972G

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