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BJOC - Natural products in synthesis and biosynthesis

Natural product synthesis/biosynthesis, Biological chemistry and enzymology, Metabolic engineering.

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Natural Product Synthesis – The Bray Research Group

Spongistatin 2 An improved route to the EF fragment of the spongistatins has been developed and employed in a synthesis of spongistatin 2. The C48–C51 diene side chain, which lacks the chlorine substituent present in spongistatin 1, presented some compatibility issues during target assembly. These were overcome by implementing a late stage Stille cross coupling to construct the diene portion of the natural product. See: H. Kraus, A. Français, M. O’Brien, J.R. Frost, A. Diéguez-Vázquez, A. Polara, N. Baricordi, R. Horan, D-S. Hsu, T. Tsunoda, S.V. Ley, 2013, , 1989-1994.

Organic chemistry of marine natural products, synthesis, NMR, and biomedical applications

This review is an updated and expanded version of a paper that was published in this journal in 1997. The time frame has been extended in both directions to include the 22 years from 1981 to 2002, and a new secondary subdivision related to the natural product source but applied to formally synthetic compounds has been introduced, using the concept of a “natural product mimic” or “NM” to join the original primary divisions. From the data presented, the utility of natural products as sources of novel structures, but not necessarily the final drug entity, is still alive and well. Thus, in the area of cancer, the percentage of small molecule, new chemical entities that are nonsynthetic has remained at 62% averaged over the whole time frame. In other areas, the influence of natural product structures is quite marked, particularly in the antihypertensive area, where of the 74 formally synthetic drugs, 48 can be traced to natural product structures/mimics. Similarly, with the 10 antimigraine drugs, seven are based on the serotonin molecule or derivatives thereof. Finally, although combinatorial techniques have succeeded as methods of optimizing structures and have, in fact, been used in the optimization of a number of recently approved agents, we have not been able to identify a combinatorial compound approved as a drug in this time frame.

Biomimetic Synthesis of Natural and â Unnaturalâ …

One field that is of particular interest is the use of a biomimetic approach towards the synthesis of complex natural products.

(–)-Hennoxazole A The syntheses of natural products O-methyl siphonazole and (–)-hennoxazole A were accomplished using a combination of batch and flow procedures. Key oxazole-containing fragments were prepared using solid-supported reagents and flow technologies to facilitate the overall syntheses of these molecules and highlight the advantages of incorporating enabling technologies into natural product synthesis. See: A. Fernández, Z.G. Levine, M. Baumann, S. Sulzer-Mossé, C. Sparr, S. Schläger, A. Metzger, I.R. Baxendale, S.V. Ley, 2013, , 514-518.

Spirangien A methyl ester and spirodienal A Over the past decade, the integration of synthetic chemistry with flow processing has resulted in a powerful platform for molecular assembly that is making an impact throughout the chemical community. We have demonstrated the extension of these tools to encompass complex natural product synthesis by developing a number of novel flow-through processes for reactions commonly encountered in natural product synthesis programs to achieve the first total synthesis of spirodienal A and the preparation of spirangien A methyl ester. Highlights of the synthetic route include an iridium-catalyzed hydrogenation, iterative Roush crotylations, gold-catalyzed spiroketalization and a late-stage cis-selective reduction. See: S. Newton, C.F. Carter, C.M. Pearson, L.C. Alves, H. Lange, P. Thansandote, S.V. Ley, Angew. Chem. Int. Edn. 2014, 53, 4915-4920.

Biomimetic Synthesis of Natural and â Unnaturalâ ..

(–)-Enniatin B A nine-step (longest linear) batch total synthesis of the cyclic hexadepsipeptide (−)-enniatin B is described. The synthesis minimizes precipitation during reaction conditions for adaptability to flow synthesis. The route was used to prepare >100 mg of the natural product. See: D.X. Hu, M. Bielitza, P. Koos, S.V. Ley, Tetrahedron Lett. 2012, 53, 4077-4079.

Isoborreverine Flow chemistry is widely used in synthetic chemistry and it has increasingly been applied to complex natural product synthesis. However, to date flow chemistry has not found a place in the area of biomimetic synthesis. Here we show the syntheses of borrerine derived alkaloids, indicating that we can use biomimetic principles in flow to prepare complex architectures in a single step. See: S.B. Kamptmann, S.V. Ley Aust. J. Chem. 2015, 68, 693-696.

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  • instructive biomimetic syntheses of natural products over ..

    Synthetic, Medicinal, Bioorganic and Biological Chemistry, Methods and Strategies in Natural Products Chemistry

  • Biomimetic Natural Product Synthesis - UNSW Science …

    16/09/2013 · Biomimetic Synthesis of Dimeric Natural Products

  • Biomimetic Natural Product Synthesis ..

    'Our efforts towards the total synthesis of complex dimeric natural products will be discussed

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Biomimetic synthesis of natural products ..

Beauvericin, bassianolide and enniatin C Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin, bassianolide and enniatin C. A reliable flow chemistry protocol was established for the coupling and macrocyclisation to form challenging N-methylated amides. This flexible approach has allowed the rapid synthesis of both natural and unnatural depsipeptides in high yields, enabling further exploration of their promising biological activity. See: D. Lücke, T. Dalton, S.V. Ley, Z.E. Wilson Chem. Eur. J. 2016, 22, 4206-4217.

Total Synthesis of Bioactive Natural Products | …

Subereomollines A and B The first total syntheses of (+)- and (-)-subereamollines A and B are reported. The enantiomeric forms of the natural products were obtained by preparative chiral HPLC separation of the corresponding racemates. See: J.W. Shearman, R. M. Myers, J.D. Brenton, S.V. Ley, Org. Biomol. Chem. 2011, 9, 62-65.

Total Synthesis of Bioactive Natural Products

2,3-Dihydropyrrolo[1,2-a]quinazolin-5(1H)-one An improved, scalable synthetic route to the quinazolinone natural product 2,3-dihydropyrrolo[1,2-]-quinazolin-5(1)-one is reported. The applicability of this method to analogue synthesis and the synthesis of related natural products is explored. Finally, reactivity of the scaffold to a variety of electrophilic reagents, generating products stereoselectively, is reported. See: C.L. Sutherell and S.V. Ley Synthesis, 2017, 49, 135-144.

Saian | Natural Clinical Skin Care

Ianthelline, 5-bromoverongamine and JBIR-44 The total syntheses of the bromotyrosine-derived natural products ianthelline, 5-bromoverongamine and JBIR-44 are described and their cytotoxic activity in a cervical cancer (HeLa) cell line and human umbilical vein endothelial cells (HUVECs) are reported. J.W. Shearman, R.M. Myers, T.M. Beale, J.D. Brenton, S.V. Ley, Tetrahedron Lett. 2010, 51, 4812-4814.

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