2022
DOI: 10.1021/acsomega.2c02116
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Toward the Total Synthesis of Alpkinidine: Synthesis of Haloquinone CE Ring System Synthons and Attempted Nucleophilic Bisannulation

Abstract: Model chemistry involving the bisannulation of 2,3-dichloro-1,4-naphthoquinone with the ester enolate derived from ethyl o -nitrophenylacetic acid, which rapid assembled the ABCD ring system of a pentacyclic pyrroloacridine, has been applied to the attempted synthesis of the marine natural product alpkinidine. The reaction of ethyl o -nitrophenylacetic acid with 6,7-dichloro-2-methylisoquinoline-1,5,8(2 H )-trione, required to extend the mode… Show more

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Cited by 3 publications
(11 citation statements)
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“…At the outset, attempts to use Michael addition reactions to couple 1,4-naphthoquinone ( 11 ) and o -nitrophenylacetonitrile ( 12 ) had been unsuccessful, producing what appeared to be oligomeric products instead of the expected hydroquinone 13 or quinone 14 adducts ( Scheme 2 ), 1 hence our prior focus on Michael substitution of haloquinones 6 and 8 ( Scheme 1 ). 2 …”
Section: Resultsmentioning
confidence: 99%
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“…At the outset, attempts to use Michael addition reactions to couple 1,4-naphthoquinone ( 11 ) and o -nitrophenylacetonitrile ( 12 ) had been unsuccessful, producing what appeared to be oligomeric products instead of the expected hydroquinone 13 or quinone 14 adducts ( Scheme 2 ), 1 hence our prior focus on Michael substitution of haloquinones 6 and 8 ( Scheme 1 ). 2 …”
Section: Resultsmentioning
confidence: 99%
“…In an effort to resurrect the general strategy of connecting the CE- and A-ring systems of potential precursors to alpkinidine, through the reaction of carbanions with quinone electrophiles, 2 the reaction of ethyl o -nitrophenylacetate ( 2 ) with isoquinolinetrione 15 2 was investigated and indeed provided a hydroquinone adduct in modest yield ( Scheme 3 ). Unfortunately, heteronuclear multiple bond correlation (HMBC) spectroscopy revealed the product to be the undesired regioisomer 16 .…”
Section: Resultsmentioning
confidence: 99%
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