Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 27, Pages 4637-4645Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900673
Keywords
Synthesis design; Nitrogen heterocycles; Natural products; Alkaloids; Azafluoranthenes; Electrocyclization
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Funding
- Ministerio de Ciencia, Tecnologia e Innovacion Productiva - Coordenacao de Aperfeioamento de Pessoal de Nivel Superior (MINCyT-CAPES) [BR-06/019]
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET) [3294]
- Agencia Nacional de Promocion Cientifica y Tecnologica (ANPCyT) [06-38165]
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The synthesis of 2-methyltriclisine, an unnatural analog of the azafluoranthene alkaloid triclisine, is reported. The synthesis was achieved in 10 steps and 21% overall yield from 2-bromo-3,4-dimethoxybenzaldehyde, through the intermediacy of 3,4-dimethoxyfluoren-9-one. Construction of the heterocyclic ring entailed the para-Claisen rearrangement of an allyl-4-fluorenyl ether, followed by isomerization of the resulting 2-allylfluoren-9-one and a microwave-assisted electrocyclization of the aza 6 pi-electron system formed by oximation of its carbonyl function. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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