Mapping Out Biogenetic Hypotheses by Chemical Synthesis
Synthesis of natural products via their postulated or established biosynthetic intermediates ('biomimetic synthesis' or 'bio-inspired synthesis') has the power to identify both yet undiscovered intermediates and undiscovered mechanistic pathways for their formation. In t...
| Main Authors: | , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
2017-12-01
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| Series: | CHIMIA |
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| Online Access: | https://www.chimia.ch/chimia/article/view/1692 |
| _version_ | 1819278733692895232 |
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| author | Raphael Liffert Karl Gademann |
| author_facet | Raphael Liffert Karl Gademann |
| author_sort | Raphael Liffert |
| collection | DOAJ |
| description |
Synthesis of natural products via their postulated or established biosynthetic intermediates ('biomimetic synthesis' or 'bio-inspired synthesis') has the power to identify both yet undiscovered intermediates and undiscovered mechanistic pathways for their formation. In this account,
we report on our recent studies on unusual hypotheses for biosynthetic transformations, such as a late-stage aldol reaction (periconianone A), benzilic acid rearrangement (taiwaniaquinone H), a redox-neutral light-driven C–H activation (taiwaniaquinol A and cyclocoulterone), a hetero
Diels-Alder reaction (obtusinones), aziridinium chemistry (Securinega alkaloids), and a [3+2] nitrone olefin cycloaddition (virosaine A). All these studies provided evidence on the molecular level for the feasibility of these transformations, and suggest that further studies investigating the relevance of these hypotheses in biological systems are warranted.
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| first_indexed | 2024-12-24T00:16:42Z |
| format | Article |
| id | doaj.art-4309b5d1497340858a6360e68466bcbb |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-12-24T00:16:42Z |
| publishDate | 2017-12-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-4309b5d1497340858a6360e68466bcbb2022-12-21T17:24:43ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242017-12-01711210.2533/chimia.2017.841Mapping Out Biogenetic Hypotheses by Chemical SynthesisRaphael Liffert0Karl Gademann1Department of Chemistry University of Zurich Winterthurerstrasse 190, CH-8057 Zurich, SwitzerlandDepartment of Chemistry University of Zurich Winterthurerstrasse 190, CH-8057 Zurich, Switzerland. karl.gademann@uzh.ch Synthesis of natural products via their postulated or established biosynthetic intermediates ('biomimetic synthesis' or 'bio-inspired synthesis') has the power to identify both yet undiscovered intermediates and undiscovered mechanistic pathways for their formation. In this account, we report on our recent studies on unusual hypotheses for biosynthetic transformations, such as a late-stage aldol reaction (periconianone A), benzilic acid rearrangement (taiwaniaquinone H), a redox-neutral light-driven C–H activation (taiwaniaquinol A and cyclocoulterone), a hetero Diels-Alder reaction (obtusinones), aziridinium chemistry (Securinega alkaloids), and a [3+2] nitrone olefin cycloaddition (virosaine A). All these studies provided evidence on the molecular level for the feasibility of these transformations, and suggest that further studies investigating the relevance of these hypotheses in biological systems are warranted. https://www.chimia.ch/chimia/article/view/1692Biomimetic chemistryBiosynthesisNatural productsOrganic synthesis |
| spellingShingle | Raphael Liffert Karl Gademann Mapping Out Biogenetic Hypotheses by Chemical Synthesis CHIMIA Biomimetic chemistry Biosynthesis Natural products Organic synthesis |
| title | Mapping Out Biogenetic Hypotheses by Chemical Synthesis |
| title_full | Mapping Out Biogenetic Hypotheses by Chemical Synthesis |
| title_fullStr | Mapping Out Biogenetic Hypotheses by Chemical Synthesis |
| title_full_unstemmed | Mapping Out Biogenetic Hypotheses by Chemical Synthesis |
| title_short | Mapping Out Biogenetic Hypotheses by Chemical Synthesis |
| title_sort | mapping out biogenetic hypotheses by chemical synthesis |
| topic | Biomimetic chemistry Biosynthesis Natural products Organic synthesis |
| url | https://www.chimia.ch/chimia/article/view/1692 |
| work_keys_str_mv | AT raphaelliffert mappingoutbiogenetichypothesesbychemicalsynthesis AT karlgademann mappingoutbiogenetichypothesesbychemicalsynthesis |