Total synthesis of the fumiquinazoline alkaloids: solution-phase studies.
Biomimetic total syntheses of glyantrypine, fumiquinazoline F, fumiquinazoline G, and fiscalin B were achieved in four steps from tryptophan methyl ester. In the key step, the anthranilamide residue in a linear tripeptide is dehydrated to a benzoxazine by reaction with triphenylphosphine, iodine, and a tertiary amine. The benzoxazines subsequently undergo rearrangement to the natural products via an amidine intermediate. This dehydrative oxazine to quinazoline route is applicable to a broad range of N-acylanthranilamides, including sterically hindered cases.
Wang
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Institute of Molecular and Cell Biology, National University of Singapore, 30 Medical Drive, Singapore 117609.
Ganesan
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A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D005658:Fungi / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013373:Substance P / Q000037:antagonists & inhibitors; D014364:Tryptophan / Q000031:analogs & derivatives*; D062367:ortho-Aminobenzoates / Q000737:chemistry / Q000378:metabolism
D000470:Alkaloids; D000970:Antineoplastic Agents; D011799:Quinazolines; D062367:ortho-Aminobenzoates; D013373:Substance P; D014364:Tryptophan