ArticleOrganic chemistry frontiers : an international journal of organic chemistry2015
Syntheses of Sceptrins and Nakamuric Acid and Insights into the Biosyntheses of Pyrrole-Imidazole Dimers.
Article in Organic chemistry frontiers : an international journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Marine alkaloids as bioactive agents against protozoal neglected tropical diseases and malaria.Natural product reports · 2021Review
- Total Synthesis of (±)-Sceptrin.Organic letters · 2020Article
- Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.Tetrahedron · 2018Article
- Natural products as inspiration for the development of new synthetic methods.Journal of the Chinese Chemical Society. Zhongguo hua xue hui (Taipei, Taiwan) · 2018Article
- Marine sponge alkaloids as a source of anti-bacterial adjuvants.Bioorganic & medicinal chemistry letters · 2016Article
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Authors and funding
6 authors.
Funding
Abstract
Sceptrins and nakamuric acid are structurally unique antibiotics isolated from marine sponges. Recent studies suggest that the biosynthesis of these dimeric pyrrole-imidazole alkaloids involves a single-electron transfer (SET)-promoted [2+2] cycloaddition to form their cyclobutane core skeletons. We describe herein the biomimetic syntheses of racemic sceptrin and nakamuric acid. We also report the asymmetric syntheses of sceptrin, bromosceptrin, and dibromosceptrin in their natural enantiomeric form. We further provide mechanistic insights into the pathway selectivity of the SET-promoted [2+2] and [4+2] cycloadditions that lead to the divergent formation of the sceptrin and ageliferin core skeletons. Both the [2+2] and [4+2] cycloadditions are stepwise reactions, with the [2+2] pathway kinetically and thermodynamically favored over the [4+2] pathway. For the [2+2] cycloaddition, the dimerization of pyrrole-imidazole monomers is rate-limiting, whereas for the [4+2] cycloaddition, the cyclization is the slowest step.
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Registered trials
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