Pyrones. IX. Synthetic approaches to the fungal metabolite phacidin and its derivatives | Zendy

G. A. POULTON | Zendy; Terry D. Cyr | Zendy

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Pyrones. 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.

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