Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products.
[reaction: see text] Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)-alpha-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.
Fischer
Joshua
J
Research School of Chemistry, Australian National University, Canberra ACT 0200, Australia.
Reynolds
Aaron J
AJ
Sharp
Lisa A
LA
Sherburn
Michael S
MS
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000494:pharmacology; D005609:Free Radicals / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D018922:HL-60 Cells / Q000187:drug effects; D006801:Humans; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D001688:Biological Products; D005609:Free Radicals; D005663:Furans; D017705:Lignans; D013764:Tetrahydronaphthalenes; C421915:conidendrin; C068935:matairesinol; C071942:arctigenin