Synthetic studies toward inducamide C.

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. A second-generation approach involved dealkylation of O-isopropylinducamide C, but the same oxepanoindole formed via rearrangement of the proposed inducamide C structure. Computational studies validate preferential formation of the oxepanoindole and the lactone in O-isopropylinducamide C is susceptible to nucleophilic attack. Thus, inducamide C is either highly unstable or in need of structural revision.

Synthesis of Inducamides A and B.

The 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. The spectroscopic data and optical rotation for each synthetic sample confirm the structures of these silent secondary metabolites and their biosynthesis from l-tryptophan.

University rural health clubs: nurturing the future Australian rural workforce.

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. The NRHN and its constituent clubs run a variety of activities to promote rural careers to both school-aged and university students. These have included events at local, state and national levels. ISSUES: The purpose of the present article is to describe the roles and activities of RHC and the NRHN as they aim to contribute towards developing a sustainable rural workforce. Key features of RHC and the NRHN are: (1) providing positive rural experiences; (2) peer promotion of rural health; (3) personal and professional development; (4) providing a volunteer workforce for rural health initiatives; and (5) cross-disciplinary interaction. The NRHN is currently investigating methods to quantify the impact of the RHC on the career choices of potential rural health professionals. LESSONS LEARNED: The NRHN and its constituent clubs are student-driven initiatives occupying a unique place in addressing the rural workforce shortage. Although little formal evidence exists for their success, the issues raised in this article illustrate their importance and broader benefits in this field.