Towards the total synthesis of alpkinidine Louisa Tham and Matthew Piggott The University of Western Australia, Australia
Alpkinidine (1) is a marine alkaloid from the sponge Xestospongia carbonaria (Figure 1) . 1 The unique, highly condensed structure of this bisannulated pyrroloacridine, and its cytotoxicity, have attracted several synthetic efforts, but so far without success. 2-4 Synthesis is essential for comprehensive characterisation of both the structure and biological activity of the natural product.
Figure 1. Marine sponge Xestospongia carbonaria and its metabolite alpkinidine (I). 5 This poster will report on the reactivity of methylamino-quinones II and -anilines III with N-Boc-isatin IV to rapidly assemble the B and D rings of alpkinidine (I) and related model compounds (e.g. VII).
References 1. P. Crews et al ., “Structures and cytotoxic properties of sponge-derived bisannulated acridines” J. Org. Chem., 67 , 9384, (2002). 2. M. Buccini, “Part I. The total synthesis of epi-antrodioxolanone Part II. Quinones as synthons for polycyclic, heteroaromatic natural products” The University of Western Australia, Doctor of Philosophy, (2017). 3. F. Dhoro, “Studies on the total synthesis of polycyclic aromatic alkaloids” The University of Western Australia, Doctor of Philosophy, (2014). 4. P. Volvoikar et al. , “A concise approach for the synthesis of the ABCD ring system of alpkinidine” ChemistrySelect, 4 , 4283, (2019). 5. C. Freeman, “ Xestospongia carbonaria ” Smithsonian Tropical Research Institute (2008). Available from: https://biogeodb.stri. si.edu/bioinformatics/dfm/metas/view/13909
P73F
© The Author(s), 2023
Made with FlippingBook Learn more on our blog