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

Research paper by Constantinos C Tsangarakis, Ioannis N IN Lykakis, Manolis M Stratakis

Indexed on: 07 Mar '08Published on: 07 Mar '08Published in: Journal of Organic Chemistry



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.