期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 69, 期 7, 页码 2461-2468出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo035778s
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Aromatic bisabolene derivatives were prepared by two methods involving cross-coupling of organozine 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)Cl-2 as catalyst. Coupling of arylzinc halides with alkenyl triflate 16 using Pd(PPh3)(4) catalyst provided a number of bisabolene derivatives and led to syntheses of dehydro-alpha-curcumene (2), (+/-)- curcuphenol (3), and (+/-)-elvirol (13). A high-yield synthesis of the (+/-)-heliannuol D precursor 29 is also reported using this method.
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