170235-99-1Relevant articles and documents
Synthesis of Aromatic Bisabolene Natural Products via Palladium-Catalyzed Cross-Couplings of Organozine Reagents
Vyvyan, James R.,Loitz, Celeste,Looper, Ryan E.,Mattingly, Cheryl S.,Peterson, Emily A.,Staben, Steven T.
, p. 2461 - 2468 (2007/10/03)
Aromatic bisabolene derivatives were prepared by two methods involving cross-coupling of organozinc reagents. The first synthesis of (±)-glandulone A (10), as well as syntheses of (± )-curcuhydroquinone (8) and (±)-curcuquinone (9), were accomplished via coupling of a secondary alkyl zinc reagent (1,5-dimethyl-4-hexenylzinc halide, 18) to protected bromohydroquinones using Pd(dppf)Cl2 as catalyst. Coupling of arylzinc halides with alkenyl triflate 16 using Pd(PPh 3)4 catalyst provided a number of bisabolene derivatives and led to syntheses of dehydro-α-curcumene (2), (±)-curcuphenol (3), and (±)-elvirol (13). A high-yield synthesis of the (±)-heliannuol D precursor 29 is also reported using this method.
A FACILE SYNTHESIS OF 4-ARYL-5-HYDROXY-(2E)-PENTENOATE DERIVATIVES AND ITS APPLICATIONS TO THE FIRST SYNTHESIS OF (+/-)-CURUCUDIOL, (+/-)-CURCUHYDROQUINONE AND (+/-)-CURCUQUINONE
Ono, Machiko,Yamamoto, Yasuo,Todoriki, Reiko,Akita, Hiroyuki
, p. 181 - 186 (2007/10/02)
The first syntheses of three kinds of bisabolane sesquiterpenes, (+/-)-curcudiol (29), (+/-)-curcuhydroquinone (40) and (+/-)-curcuquinone (41) were achieved based on the BF3*Et2O catalyzed reaction of (+/-) methyl 4,5-epoxy-(2E)-pentenoate (1) and polyme