An efficient synthesis of (+/-)-grandisol featuring 1,5-enyne metathesis.

ABSTRACT: 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.

SUBMITTER: Graham TJ 

PROVIDER: S-EPMC2798917 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature