An efficient synthesis of (+/-)-grandisol featuring 1,5-enyne metathesis.
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.
Graham
Thomas J A
TJ
Department of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, USA.
Gray
Erin E
EE
Burgess
James M
JM
Goess
Brian C
BC
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
D000480:Alkynes; D012724:Sex Attractants; D013729:Terpenes; C013009:grandisol