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On the Front Cover of Issue 19
Lucidene is a natural product isolated from the root bark of Uvaria lucidassp. The co-isolation of ?-humulene from the same species led to speculation that lucidene is the product of two consecutive, inverse demand hetero Diels-Alder cycloadditions of ? -humulene with two equivalents of o-quinone methide. A biomimetic approach to the synthesis of lucidene is portrayed, with the elimination of water from hydroxymethyl-orcinol, providing the driving force for the generation of the o-quinone methide.
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, Org. Biomol. Chem., 2005, 3, 3488
DOI: 10.1039/b508972g
