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Synthesis of nectriapyrone
Author(s) -
Abramson Hanley N.,
Wormser Henry C.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180227
Subject(s) - chemistry , decarboxylation , dehydrogenation , hydrolysis , methylation , metabolite , condensation , organic chemistry , stereochemistry , catalysis , biochemistry , physics , thermodynamics , gene
A totally synthetic route to the antibacterial fungal metabolite nectriapyrone ( 1 ) has been achieved by condensation of methylmalonyl dichloride with ethyl trans ‐4‐methyl‐3‐oxo‐4‐hexenoate followed by hydrolysis, decarboxylation, and methylation of the resulting 3‐methyl‐4‐hydroxy‐5‐carbethoxy‐6‐( trans ‐1‐methyl‐1‐propenyl)‐2‐pyrone. Exploration of an alternate scheme involving the dehydrogenation of 6‐substituted‐4‐methoxy‐5,6‐dihydro‐2‐pyrones, prepared by Reformatsky reaction of ethyl γ‐bromo‐β‐methoxycrotonate with various aldehydes, was abandoned since it did not appear to have general applicability to the preparation of nectriapyrone and its analogs.