SYNTHESIS OF CERPEGIN

SYNTHESIS OF CERPEGIN

Cerpegin (1), a new pyridone alkaloid, was synthesized starting from the Michael reaction of phenylthioacetonitrile (2) and 2-methoxycarbonyl-4, 4-dimethyl-2-buten-4-olide (3) in five steps. Catalytic hydrogenation of a nitrile group in the presence of a conjugated carbon-carbon double bond was perf...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1994/03/15, Vol.42(3), pp.715-717
Hauptverfasser: MATSUO, Keizo, ARASE, Takahiko
Format: Artikel
Sprache:eng
Schlagworte:
catalytic hydrogenation
cerpegin
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Michael reaction
Organic chemistry
phenylthioacetonitrile
Preparations and properties
pyridone alkaloid
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Beschreibung
Zusammenfassung:Cerpegin (1), a new pyridone alkaloid, was synthesized starting from the Michael reaction of phenylthioacetonitrile (2) and 2-methoxycarbonyl-4, 4-dimethyl-2-buten-4-olide (3) in five steps. Catalytic hydrogenation of a nitrile group in the presence of a conjugated carbon-carbon double bond was performed by addition of 1 eq of conc. HCl.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.42.715