Ga(III)-catalyzed cycloisomerization approach to (+/-)-icetexone and (+/-)-epi-icetexone.
A Ga(III)-catalyzed cycloisomerization reaction provides expedient access to a benzannulated cycloheptadiene bearing a cyano group, which has been applied to the syntheses of several icetexane diterpenoids including icetexone and epi-icetexone. Key to the synthesis is a novel in situ generated diazene rearrangement.
Cortez
Felipe de Jesus
Fde J
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Sarpong
Richmond
R
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005682:Gadolinium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes; C512853:icetexone; D005682:Gadolinium