Seminar: A/Prof Jonathan George - Biomimetic Synthesis of Natural Products

Thursday, 19 April 2018 - 12:00pm – Thursday, 19 April 2018 - 1:00pm  |  CHEMSCI M10

Speaker: A/Prof Jonathan George

In the first half of my talk, I will describe the development of biomimetic cascade reactions based on the natural products hyperjaponol C [1] and verrubenzospirolactone [2].

In the second half of my talk, I will present a more detailed discussion of naphthoquinone meroterpenoid antibiotics that have been isolated from marine and soil strains of Streptomyces bacteria, including merochlorins, napyradiomycins, naphterpins and marinones. They possess unusual aromatic oxidation patterns that are known to be biosynthesized from 1,3,6,8-tetrahydroxynaphthalene (THN). We propose that chlorination of THN derivatives by vanadium-dependent chloroperoxidase (VCPO) enzymes is key to these biosynthetic pathways. This hypothesis has inspired biomimetic syntheses of merochlorin A,[3] the napyradiomycins,[4] and the naphterpin/marinone family.

References: 1) H. C. Lam, J. T. J. Spence, J. H. George, Angew. Chem. Int. Ed.  2016, 55, 10368. 2) H. C. Lam, H. P. Pepper, J. H. George, Angew. Chem. Int. Ed.  2017, 56, 8532. 3) H. P. Pepper, J. H. George, Angew. Chem. Int. Ed.  2013, 52, 12170. 4) Z. D. Miles, S. Diethelm, H. P. Pepper, D. M. Huang, J. H. George, B. S. Moore, Nat. Chem.  2017, 9, 1235.

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