Total Synthesis of (±)-Porosin, a Neolignan from Ocotea porosa and Urbanodendron verrucosum (Lauraceae)
Matsumoto, T; Takeda, Y; Oiwamoto, M; Fujii, K; Kishida, M; Shibutani, H; Imai, S
| HERO ID | 4932934 |
|---|---|
| In Press | No |
| Year | 1995 |
| Title | Total Synthesis of (±)-Porosin, a Neolignan from Ocotea porosa and Urbanodendron verrucosum (Lauraceae) |
| Authors | Matsumoto, T; Takeda, Y; Oiwamoto, M; Fujii, K; Kishida, M; Shibutani, H; Imai, S |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 43 |
| Issue | 12 (1995) |
| Page Numbers | 2099 |
| Abstract | Veratraldehyde was condensed with methyl 2-chloropropanoate to give a glycidic ester. This was hydrolyzed with aqueous sodium hydroxide and the resulting sodium salt was treated with lead(IV) tetraacetate to give 1-acetoxy-1-(3, 4-dimethoxyphenyl)propan-2-one (13). Condensation of 13 with dimethyl malonate, followed by acidic hydrolysis and sodium borohydride reduction afforded (2R*, 3S*, 4R*)-4-(3, 4-dimethoxyphenyl)-2-methoxycarbonyl-3-methyl-4-butanolide (7a). The γ-lactone 7a was then converted into 5'-demethoxyporosin (10) by means of a series of reactions : Michael reaction with methyl vinyl ketone, elimination of the methoxycarbonyl group, acetalization, allylation, deacetalization, and intramolecular aldol reaction. Introduction of a hydroxyl group at the C-5' position in 10, followed by methylation with diazomethane afforded racemic porosin. The synthetic porosin was further converted into 5-demethoxymegaphone acetate. |
| Wosid | WOS:A1995TM64700012 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | synthesis; (+/-)-porosin; neolignan; Ocotea porosa; Urbanodendron verrucosum |