Journal of Organic Chemistry 2008-04-04

Zeolite NaY-promoted cyclization of farnesal: a short route to nanaimoal.

Constantinos Tsangarakis, Ioannis N Lykakis, Manolis Stratakis

Index: J. Org. Chem. 73(7) , 2905-8, (2008)

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Abstract

The sesquiterpene nanaimoal was synthesized in 21% overall yield and in a biomimetic manner. As a key step, the acid-catalyzed cyclization of farnesal under zeolite NaY confinement conditions was used. The intrazeolite cyclization of farnesal affords as major product a double-bond isomer of nanaimoal, via a novel diastereoselective tandem 1,5-diene cyclization/Prins-type reaction.