Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores
Diastereodivergent synthesis of octahydrophenanthridinone and octahydrophenanthridine skeletons, structural motifs often found in biologically active natural products, is described. We previously reported a total synthesis of a pancratistatin analog using novel octahydrophenanthridinone construction...
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| Language: | English |
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MDPI AG
2025-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/2/371 |
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| author | Chunzhao Sun Hiromichi Nishikawa Tsubasa Inokuma Ken-ichi Yamada |
| author_facet | Chunzhao Sun Hiromichi Nishikawa Tsubasa Inokuma Ken-ichi Yamada |
| author_sort | Chunzhao Sun |
| collection | DOAJ |
| description | Diastereodivergent synthesis of octahydrophenanthridinone and octahydrophenanthridine skeletons, structural motifs often found in biologically active natural products, is described. We previously reported a total synthesis of a pancratistatin analog using novel octahydrophenanthridinone construction. In this study, we examined the generality of our method and its extension to octahydrophenanthridine formation. Conjugate addition of diarylcuprates to nitrosocyclohexenes, which were generated in situ from 2-chlorocyclohexanone oximes, provided 2-arylcyclohexanone oximes. Subsequent reduction of the oxime moiety gave <i>cis</i>- and <i>trans</i>-configured amines. Both amines were separately converted into the corresponding octahydrophenanthridinones and octahydrophenanthridines via hexahydrophenanthridine intermediates. |
| format | Article |
| id | doaj-art-38e7016753744fb4b932a6be1a19a20f |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-38e7016753744fb4b932a6be1a19a20f2025-01-24T13:43:48ZengMDPI AGMolecules1420-30492025-01-0130237110.3390/molecules30020371Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine CoresChunzhao Sun0Hiromichi Nishikawa1Tsubasa Inokuma2Ken-ichi Yamada3Graduate School of Pharmaceutical Sciences, Tokushima University, Shomachi 770-8505, Tokushima, JapanGraduate School of Pharmaceutical Sciences, Tokushima University, Shomachi 770-8505, Tokushima, JapanGraduate School of Pharmaceutical Sciences, Tokushima University, Shomachi 770-8505, Tokushima, JapanGraduate School of Pharmaceutical Sciences, Tokushima University, Shomachi 770-8505, Tokushima, JapanDiastereodivergent synthesis of octahydrophenanthridinone and octahydrophenanthridine skeletons, structural motifs often found in biologically active natural products, is described. We previously reported a total synthesis of a pancratistatin analog using novel octahydrophenanthridinone construction. In this study, we examined the generality of our method and its extension to octahydrophenanthridine formation. Conjugate addition of diarylcuprates to nitrosocyclohexenes, which were generated in situ from 2-chlorocyclohexanone oximes, provided 2-arylcyclohexanone oximes. Subsequent reduction of the oxime moiety gave <i>cis</i>- and <i>trans</i>-configured amines. Both amines were separately converted into the corresponding octahydrophenanthridinones and octahydrophenanthridines via hexahydrophenanthridine intermediates.https://www.mdpi.com/1420-3049/30/2/371octahydrophenanthridinoneoctahydrophenanthridinealkaloidstereodivergent synthesisarylationorganocuprate |
| spellingShingle | Chunzhao Sun Hiromichi Nishikawa Tsubasa Inokuma Ken-ichi Yamada Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores Molecules octahydrophenanthridinone octahydrophenanthridine alkaloid stereodivergent synthesis arylation organocuprate |
| title | Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores |
| title_full | Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores |
| title_fullStr | Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores |
| title_full_unstemmed | Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores |
| title_short | Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores |
| title_sort | diastereodivergent construction of octahydrophenanthridinone and octahydrophenanthridine cores |
| topic | octahydrophenanthridinone octahydrophenanthridine alkaloid stereodivergent synthesis arylation organocuprate |
| url | https://www.mdpi.com/1420-3049/30/2/371 |
| work_keys_str_mv | AT chunzhaosun diastereodivergentconstructionofoctahydrophenanthridinoneandoctahydrophenanthridinecores AT hiromichinishikawa diastereodivergentconstructionofoctahydrophenanthridinoneandoctahydrophenanthridinecores AT tsubasainokuma diastereodivergentconstructionofoctahydrophenanthridinoneandoctahydrophenanthridinecores AT kenichiyamada diastereodivergentconstructionofoctahydrophenanthridinoneandoctahydrophenanthridinecores |