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  • An efficient approach to dihydrofurocoumarins via palladium-catalyzed annulation of 1,3-dienes by o-iodoacetoxycoumarins.

An efficient approach to dihydrofurocoumarins via palladium-catalyzed annulation of 1,3-dienes by o-iodoacetoxycoumarins.

The Journal of organic chemistry (2003-08-05)
Roman V Rozhkov, Richard C Larock
ABSTRACT

The palladium-catalyzed annulation of 1,3-dienes by o-iodoacetoxycoumarins provides an efficient method for the synthesis of biologically interesting dihydrofurocoumarins. The presence of the acetyl group on the phenolic oxygen and the use of silver carbonate as a base are crucial for this process. This reaction is very general and regio- and stereoselective, and a wide variety of terminal, cyclic, and internal 1,3-dienes can be utilized. Derivatization of the annulation products provides an efficient approach to numerous analogues of natural products.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Silver carbonate on Celite®, extent of labeling: ~50 wt. % loading
Sigma-Aldrich
Silver carbonate, purum p.a., ≥99.0% (AT)
Sigma-Aldrich
Silver carbonate, 99%