title: 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.
authors: Department of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, USA.
authors: Thomas J A
authors: TJ
authors: Graham
authors: Erin E
authors: EE
authors: Gray
authors: James M
authors: JM
authors: Burgess
authors: Brian C
authors: BC
authors: Goess
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D012724:Sex Attractants; D013729:Terpenes; C013009:grandisol