Total syntheses of the benzodiazepine alkaloids circumdatin F and circumdatin C |
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Authors: | Witt A Bergman J |
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Affiliation: | Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and S?dert?rn University College, Novum Research Park, SE-141 57 Huddinge, Sweden. |
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Abstract: | 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. |
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