Methodology for the Synthesis of Nitrogen Heterocycles

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DESCRIPTION (provided by applicant): The long term objectives of this research program are to develop a strategy for the synthesis of the marine antitumor alkaloid nakadomarin. Also it is intended to investigate the synthesis of the marine indole alkaloids, securine A/B, securamine A/B and chartelline A using a putative biomimetic strategy. The initial targets will lack the bromine atoms in the benzenoid ring. The synthesis of a range of antitumor antibiotics with the common core known as tetrahydroquinolines, including lemonomycin and saframycin A will be studied. New synthetic strategies and methodology will be studied in the course of these investigations, in particular the trapping of sulfonium ions by azide to give, after hydrolysis, lactams. The synthetic intermediates, particularly as they more closely resemble the natural products, will be screened to assess biological activity.