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The synthesis of racemic cedarmycin B,an antibiotic from Streptomyces sp.TP-A0456 was achieved firstly fromγ- butyrolactone.The key step was a Barbier-type addition of 3-bromomethyl-5H-furan-2-one to formaldehyde mediated by zinc, which afforded the soleγ-addition product 4-hydroxymethyl-3-methylene-dihydrofuran-2-one.The final compound was confirmed by ~1H NMR,~(13)C NMR and HRMS.
The synthesis of racemic cedarmycin B, an antibiotic from Streptomyces sp. TP-A0456 was achieved from γ-butyrolactone. The key step was a Barbier-type addition of 3-bromomethyl-5H-furan-2-one to formaldehyde mediated by zinc, which afforded the sole gamma-addition product 4-hydroxymethyl-3-methylene-dihydrofuran-2-one. The final compound was confirmed by ~ 1H NMR, ~ (13) C NMR and HRMS.