The alkaloid inducamide C is proposed to contain a very rare benzoxazepine ring. Herein, we report that the benzoxazepine ring in inducamide C is unstable and prone to rearrangement, indicating that structural revision of the natural product may be necessary. In a first-generation synthetic approach, attempts to assemble the benzoxazepine by cyclization of 4-hydroxyinducamide A led to the regioisomeric oxepanoindole, a result of the 4-hydroxyindole (C4-OH) undergoing preferential cyclization instead of the desired chlorosalicylic acid C15-OH.
View Article and Find Full Text PDFThe inducamides are a family of chlorinated alkaloids featuring an amide arising from union of an l-tryptophan to a rare chlorosalicylic acid unit, the production of which is linked to a chemically induced mutation in the RNA polymerase of Streptomyces sp. (SNC-109-M3). The synthesis of inducamides A and B has been accomplished by the coupling of 6-hydroxy-3-chloro-2-methylbenzoic acid with l-6-chlorotryptophan and l-tryptophan, respectively, followed by ester hydrolysis.
View Article and Find Full Text PDFRural Remote Health
September 2007
Context: Australian university rural health clubs (RHC) are part of a national strategy to address the rural health workforce shortage. The student members of these clubs throughout Australia comprise the National Rural Health Network (NRHN). The NRHN is a multidisciplinary body representing medical, nursing and allied health students, aiming to increase the health workforce and health outcomes for rural and remote Australians.
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