An efficient synthesis of (±)-grandisol featuring 1,5-enyne metathesis
ACS Citation
Graham, T. J. A.; Gray, E. E.; Burgess, J. M.; Goess, B. C. An efficient synthesis of (±)-grandisol featuring 1,5-enyne metathesis. J. Org. Chem. 2010, 75, 226-8.
Version of Record
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.
Source Name
Journal of Organic Chemistry
Publication Date
1-1-2010
Volume
75
Issue
1
Page(s)
331-334
Document Type
Citation
Citation Type
Article
COinS