Catalytic Cascade Reactions Inspired by Polyketide Biosynthesis
Aldol reactions belong to the most important methods for carbon–carbon bond formation and are also involved in one of the most astonishing biosynthetic processes: the biosynthesis of polyketides governed by an extraordinarily sophisticated enzymatic machinery. In contrast to the typical linear or co...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
2020-09-01
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| Series: | CHIMIA |
| Subjects: | |
| Online Access: | https://www.ingentaconnect.com/contentone/scs/chimia/2020/00000074/00000009/art00009 |
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| author | Daniel Moser Alessandro Castrogiovanni Dominik Lotter Reto M. Witzig Vincent C. Fäseke Felix C. Raps Christof Sparr |
| author_facet | Daniel Moser Alessandro Castrogiovanni Dominik Lotter Reto M. Witzig Vincent C. Fäseke Felix C. Raps Christof Sparr |
| author_sort | Daniel Moser |
| collection | DOAJ |
| description | Aldol reactions belong to the most important methods for carbon–carbon bond formation and are also involved in one of the most astonishing biosynthetic processes: the biosynthesis of polyketides governed by an extraordinarily sophisticated enzymatic machinery. In contrast to the typical linear or convergent strategies followed in chemical synthesis, this late-stage catalysis concept allows Nature to assemble intermediates that are diversified into a broad range of scaffolds, which assume various crucial biological functions. To transfer this concept to small-molecule catalysis to access products beyond the natural systems, a stepwise approach to differentiate increasingly complex substrates was followed by investigating arene-forming polyketide cyclizations. An outline of our efforts to develop and apply these concepts are presented herein. |
| first_indexed | 2024-12-12T00:15:54Z |
| format | Article |
| id | doaj.art-88f8f1d28f8f498a939675190ff03f3a |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-12-12T00:15:54Z |
| publishDate | 2020-09-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-88f8f1d28f8f498a939675190ff03f3a2022-12-22T00:44:51ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242020-09-0174969970310.2533/chimia.2020.699Catalytic Cascade Reactions Inspired by Polyketide BiosynthesisDaniel Moser0Alessandro Castrogiovanni1Dominik Lotter2Reto M. Witzig3Vincent C. Fäseke4Felix C. Raps5Christof Sparr6University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 Basel 2: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 BaselUniversity of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 Basel 2: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 BaselUniversity of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 Basel 2: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 BaselUniversity of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 Basel 2: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 BaselUniversity of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 Basel 2: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 BaselUniversity of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 Basel 2: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 BaselUniversity of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 Basel 2: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 BaselAldol reactions belong to the most important methods for carbon–carbon bond formation and are also involved in one of the most astonishing biosynthetic processes: the biosynthesis of polyketides governed by an extraordinarily sophisticated enzymatic machinery. In contrast to the typical linear or convergent strategies followed in chemical synthesis, this late-stage catalysis concept allows Nature to assemble intermediates that are diversified into a broad range of scaffolds, which assume various crucial biological functions. To transfer this concept to small-molecule catalysis to access products beyond the natural systems, a stepwise approach to differentiate increasingly complex substrates was followed by investigating arene-forming polyketide cyclizations. An outline of our efforts to develop and apply these concepts are presented herein.https://www.ingentaconnect.com/contentone/scs/chimia/2020/00000074/00000009/art00009aldol condensationatropisomersbiomimetic synthesislate-stage catalysisstereoselectivity |
| spellingShingle | Daniel Moser Alessandro Castrogiovanni Dominik Lotter Reto M. Witzig Vincent C. Fäseke Felix C. Raps Christof Sparr Catalytic Cascade Reactions Inspired by Polyketide Biosynthesis CHIMIA aldol condensation atropisomers biomimetic synthesis late-stage catalysis stereoselectivity |
| title | Catalytic Cascade Reactions Inspired by Polyketide Biosynthesis |
| title_full | Catalytic Cascade Reactions Inspired by Polyketide Biosynthesis |
| title_fullStr | Catalytic Cascade Reactions Inspired by Polyketide Biosynthesis |
| title_full_unstemmed | Catalytic Cascade Reactions Inspired by Polyketide Biosynthesis |
| title_short | Catalytic Cascade Reactions Inspired by Polyketide Biosynthesis |
| title_sort | catalytic cascade reactions inspired by polyketide biosynthesis |
| topic | aldol condensation atropisomers biomimetic synthesis late-stage catalysis stereoselectivity |
| url | https://www.ingentaconnect.com/contentone/scs/chimia/2020/00000074/00000009/art00009 |
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