First Total Synthesis of Bauerine C

The first total synthesis of Bauerine C, a unique indoloquinazoline alkoloid, has been achieved from readily available 2,3-dichloroaniline. The key step is the Japp-Klingmann condensation between 2,3-dichloroaniline and ethyl-2-acetyl-5-phthalimido pentanoate to get 3-[(2,3-dichlorophenyl)-hydrozono...

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Bibliographic Details
Published in:Synthetic communications 2007-11, Vol.37 (24), p.4313-4318
Main Authors: Lingam, Y., Muralimohan Rao, D., Bhowmik, Dipal R., Islam, Aminul
Format: Article
Language:English
Subjects:
Bauerine C
cyclization
indoloquinazoline alkaloid
Japp-Klingmann condensation
methylation
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Summary:The first total synthesis of Bauerine C, a unique indoloquinazoline alkoloid, has been achieved from readily available 2,3-dichloroaniline. The key step is the Japp-Klingmann condensation between 2,3-dichloroaniline and ethyl-2-acetyl-5-phthalimido pentanoate to get 3-[(2,3-dichlorophenyl)-hydrozono]-pipiridin-2-one, which cyclizes to 7,8-dichloro-2,3,4,9-tetrahydro-β-carbolin-1-one, which can be methylated by dimethyl sulphate to give 7,8-dichloro-9-methyl 2,3,4,9-tetrahydro-β-carbolin-1-one. This N-methyl derivative is then subjected to dehydrogenation with 2,3-dichloro-5,6-dicayano-1,4-benzoquinone (DDQ) to give the target compound Bauerine C.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910701575426