The synthesis of ventiloquinone L, the monomer of cardinalin 3.
Readily available ethyl-4-acetoxy-6,8-dimethoxynaphthalene-2-carboxylate was converted into 1-[3-allyl-4-(benzyloxy)-6,8-dimethoxy-2-naphthyl)-1-ethanol in seven steps. Subjection of this compound to Wacker oxidation conditions provided 5-benzyloxy-7,9-dimethoxy-1,3-dimethyl-1H-benzo[g]isochromene in good yield. Hydrogenation of the isochromene afforded (+/-)-cis-7,9-dimethoxy-1,3-dimethyl-1H-benzo[g]isochroman-5-ol as the major product, which was readily converted into ventiloquinone L.
Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits, 2050, South Africa.
Edwin M
EM
Mmutlane
Joseph P
JP
Michael
Ivan R
IR
Green
Charles B
CB
De Koning
D005658:Fungi / Q000737:chemistry*; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D027823:Rhamnaceae / Q000737:chemistry*
D009285:Naphthoquinones; D011714:Pyrans; C501548:ventiloquinone 1; C501547:ventiloquinone 2; C501546:ventiloquinone 3; C501541:ventiloquinone L