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Paper

Org. Biomol. Chem., 2005, 3, 3488 - 3495, DOI: 10.1039/b508972g

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

Raphaėl Rodriguez, John E. Moses, Robert M. Adlington and Jack E. Baldwin

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.

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