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Total syntheses of the benzodiazepine alkaloids circumdatin F and circumdatin C
Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
2001 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 8, 2784-2788 p.Article in journal (Refereed) Published
Abstract [en]

Total syntheses of circumdatin F and circumdatin C, which both possess a 3H-quinazolin-4-one as well as a 1,4-benzodiazepin-5-one moiety, are described. A tripeptide derivative was synthesized as a key intermediate and dehydrated to a benzoxazine by reaction with triphenylphosphine, iodine, and a tertiary amine. The natural products were attained via rearrangements to an amidine intermediate, deprotection with 45% HBr in acetic acid, and cyclization on silica gel.

Place, publisher, year, edition, pages
2001. Vol. 66, no 8, 2784-2788 p.
National Category
Organic Chemistry
URN: urn:nbn:se:sh:diva-15860DOI: 10.1021/jo001696hISI: 000168258600034PubMedID: 11304202ScopusID: 2-s2.0-0035917331OAI: diva2:509248
Available from: 2012-03-12 Created: 2012-03-09 Last updated: 2014-04-22Bibliographically approved

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