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J Org Chem. 2004 Apr 2;69(7):2461-8.

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

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  • 1Department of Chemistry, Western Washington University, Bellingham, Washington 98225-9150, USA. vyvyan@chem.wwu.edu

Abstract

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.

PMID:
15049646
DOI:
10.1021/jo035778s
[PubMed - indexed for MEDLINE]
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