First Total Synthesis of the Cytotoxic Carbazole Alkaloid Excavatine-A and Regioselective Annulation to Pyrano[2,3-a]carbazoles and [1,4]Oxazepino[2,3,4-jk]carbazoles

dc.contributor.author	Brütting C.
dc.contributor.author	Kataeva O.
dc.contributor.author	Schmidt A.
dc.contributor.author	Knölker H.
dc.date.accessioned	2018-04-05T07:09:51Z
dc.date.available	2018-04-05T07:09:51Z
dc.date.issued	2017
dc.identifier.issn	1434-193X
dc.identifier.uri	http://dspace.kpfu.ru/xmlui/handle/net/130014
dc.description.abstract	© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim We describe the first total synthesis of the cytotoxic carbazole alkaloid excavatine-A. The carbazole framework was constructed through double C–H bond activation of a diarylamine by using our palladium(II)-catalyzed oxidative cyclization. Treatment of the intermediate 8-hydroxycarbazoles with prenal and different additives led either to pyrano[2,3-a]carbazoles or to [1,4] oxazepino[2,3,4-jk]carbazoles. The pyran annulation was investigated to determine the influence of substitution pattern, additives, and reaction time on the selectivity.
dc.relation.ispartofseries	European Journal of Organic Chemistry
dc.subject	Alkaloids
dc.subject	Carbazoles
dc.subject	Oxazepines
dc.subject	Palladium
dc.subject	Total synthesis
dc.title	First Total Synthesis of the Cytotoxic Carbazole Alkaloid Excavatine-A and Regioselective Annulation to Pyrano[2,3-a]carbazoles and [1,4]Oxazepino[2,3,4-jk]carbazoles
dc.type	Article
dc.relation.ispartofseries-issue	22
dc.relation.ispartofseries-volume	2017
dc.collection	Публикации сотрудников КФУ
dc.relation.startpage	3288
dc.source.id	SCOPUS1434193X-2017-2017-22-SID85020530327

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