An efficient synthesis of (Â±)-grandisol featuring 1,5-enyne metathesis
Graham, T. J. A.; Gray, E. E.; Burgess, J. M.; Goess, B. C. An efficient synthesis of (Â±)-grandisol featuring 1,5-enyne metathesis. J. Org. Chem. 2010, 75, 226-8.
An eight-step synthesis of (+/-)-grandisol features a key sequence involving a high-yielding, microwave-assisted enyne metathesis to yield a 1-alkenylcyclobutene that is semihydrogenated to yield a silyl-protected grandisol. Metathesis catalyst screens revealed an intriguing trend whereby substrate conversion correlated strongly with the identity of the ligands on the catalyst. In addition, new reactivity of 1-alkenylcyclobutenes toward hydrogenation is described.
Journal of Organic Chemistry