Zeolite NaY-promoted cyclization of farnesal: a short route to nanaimoal.
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.
Tsangarakis
Constantinos
C
Department of Chemistry, University of Crete, Voutes 71003, Iraklion, Greece.
Lykakis
Ioannis N
IN
Stratakis
Manolis
M
D003500:Cyclization; D005204:Farnesol / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D012964:Sodium / Q000737:chemistry*; D013237:Stereoisomerism; D017641:Zeolites / Q000737:chemistry*
D012717:Sesquiterpenes; C529555:nanaimoal; D017641:Zeolites; D005204:Farnesol; D012964:Sodium; C084519:farnesal