Total synthesis of gibbilimbols A-D.
Gibbilimbols A-D (1-4) were synthesized in 32-49% yield over four steps from commercially available starting materials. A copper-catalyzed coupling of 4-methoxyphenylmagnesium bromide with various unsaturated alkyl bromides was the key step in assembling the (long-chain alkyl)phenol skeleton.
Vyvyan
James R
JR
Department of Chemistry, Western Washington University, Bellingham, Washington 98225-9150, USA. vyvyan@chem.wwu.edu
Holst
Christian L
CL
Johnson
Allison J
AJ
Schwenk
Cheryl M
CM
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003300:Copper / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D026321:Piperaceae / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*
D010636:Phenols; C437729:gibbilimbol A; C437730:gibbilimbol B; C437731:gibbilimbol C; C437732:gibbilimbol D; D003300:Copper