Synthesis of aromatic bisabolene natural products via palladium-catalyzed cross-couplings of organozinc reagents.

نویسندگان

  • James R Vyvyan
  • Celeste Loitz
  • Ryan E Looper
  • Cheryl S Mattingly
  • Emily A Peterson
  • Steven T Staben
چکیده

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)Cl(2) 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-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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عنوان ژورنال:
  • The Journal of organic chemistry

دوره 69 7  شماره 

صفحات  -

تاریخ انتشار 2004