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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

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

Graham Thomas J A TJ   Gray Erin E EE   Burgess James M JM   Goess Brian C BC  

The Journal of organic chemistry 20100101 1

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. ...[more]

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