Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif
A concise method for the construction of dioxabicyclo[3.3.1]nonene framework has been developed. This structural motif has recently been identified in hybrid‐type pyranonaphthoquinone‐class natural products. The reaction proceeds in a stereoselective manner under mild conditions. In conjunction with...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2025-07-01
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| Series: | ChemistryEurope |
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| Online Access: | https://doi.org/10.1002/ceur.202500086 |
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| _version_ | 1849318301436477440 |
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| author | Yoshio Ando Sota Ajima Ken Ohmori |
| author_facet | Yoshio Ando Sota Ajima Ken Ohmori |
| author_sort | Yoshio Ando |
| collection | DOAJ |
| description | A concise method for the construction of dioxabicyclo[3.3.1]nonene framework has been developed. This structural motif has recently been identified in hybrid‐type pyranonaphthoquinone‐class natural products. The reaction proceeds in a stereoselective manner under mild conditions. In conjunction with this study, the scalable total syntheses of nanaomycins A and D have been achieved. Based on extensive screening of reaction conditions and nucleophiles, a plausible reaction mechanism is proposed. |
| format | Article |
| id | doaj-art-e3b887b6bacb4546a9e879d1f23f7780 |
| institution | Kabale University |
| issn | 2751-4765 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryEurope |
| spelling | doaj-art-e3b887b6bacb4546a9e879d1f23f77802025-08-20T03:50:53ZengWiley-VCHChemistryEurope2751-47652025-07-0134n/an/a10.1002/ceur.202500086Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene MotifYoshio Ando0Sota Ajima1Ken Ohmori2Department of Chemistry Institute of Science Tokyo 2‐12‐1 O‐okayama Meguro‐ku Tokyo 152‐8551 JapanDepartment of Chemistry Institute of Science Tokyo 2‐12‐1 O‐okayama Meguro‐ku Tokyo 152‐8551 JapanDepartment of Chemistry Institute of Science Tokyo 2‐12‐1 O‐okayama Meguro‐ku Tokyo 152‐8551 JapanA concise method for the construction of dioxabicyclo[3.3.1]nonene framework has been developed. This structural motif has recently been identified in hybrid‐type pyranonaphthoquinone‐class natural products. The reaction proceeds in a stereoselective manner under mild conditions. In conjunction with this study, the scalable total syntheses of nanaomycins A and D have been achieved. Based on extensive screening of reaction conditions and nucleophiles, a plausible reaction mechanism is proposed.https://doi.org/10.1002/ceur.202500086bicyclic skeletonnanaomycinsnatural productsquinonestotal synthesis |
| spellingShingle | Yoshio Ando Sota Ajima Ken Ohmori Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif ChemistryEurope bicyclic skeleton nanaomycins natural products quinones total synthesis |
| title | Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif |
| title_full | Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif |
| title_fullStr | Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif |
| title_full_unstemmed | Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif |
| title_short | Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif |
| title_sort | synthetic study on bicyclic pyranonaphthoquinone natural products construction of the dioxabicyclo 3 3 1 nonene motif |
| topic | bicyclic skeleton nanaomycins natural products quinones total synthesis |
| url | https://doi.org/10.1002/ceur.202500086 |
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