Open AccessPyrones. IX. Synthetic approaches to the fungal metabolite phacidin and its derivatives
Author(s) -
G. A. Poulton,
Terry D. Cyr
Publication year - 1982
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v82-405
Subject(s) - chemistry , metabolite , pyran , lactone , derivative (finance) , ethyl acetoacetate , dithiane , stereochemistry , organic chemistry , catalysis , biochemistry , financial economics , economics
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.