Pyrones. IX. Synthetic approaches to the fungal metabolite phacidin and its derivatives
- 15 November 1982
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 60 (22) , 2821-2829
- https://doi.org/10.1139/v82-405
Abstract
The synthesis of the antibiotic fungal metabolite phacidin 1 (4-methoxy-6-nonanoyl-2H-pyran-2-one-3-carboxaldehyde) and two related compounds is reported. Phacidin has been prepared in four steps from the readily available triacetic acid lactone (4-hydroxy-6-methyl-2H-pyran-2-one), while the decarbonylated derivative 2 and the bromo compound 3 have been synthesized utilizing a route based upon the condensation of the dianion of ethyl acetoacetate with a substituted 1,3-dithiane-2-carboxaldehyde.This publication has 4 references indexed in Scilit:
- Pyrones. VI. The total synthesis of phacidinCanadian Journal of Chemistry, 1980
- Biogenetically modeled syntheses of heptaacetate metabolites. Alternariol and lichexanthoneJournal of the American Chemical Society, 1977
- In vitro growth inhibitory studies of phacidin against some dermatophytes, opportunistic and systemic fungi, and yeasts pathogenic on manJournal of Antimicrobial Chemotherapy, 1977
- Pyrone studies—IITetrahedron, 1967