Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization
The integration of copper(I)-catalyzed three-component coupling with gold(I)-mediated 6-endo cyclization streamlines the rapid and modular assembly of the substructure of bis-tetrahydroisoquinoline (THIQ) alkaloids. The design of the key synthetic intermediate bearing a 2,3-diaminobenzofuran moiety...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.14 |
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| author | Asahi Kanno Ryo Tanifuji Satoshi Yoshida Sota Sato Saori Maki-Yonekura Kiyofumi Takaba Jungmin Kang Kensuke Tono Koji Yonekura Hiroki Oguri |
| author_facet | Asahi Kanno Ryo Tanifuji Satoshi Yoshida Sota Sato Saori Maki-Yonekura Kiyofumi Takaba Jungmin Kang Kensuke Tono Koji Yonekura Hiroki Oguri |
| author_sort | Asahi Kanno |
| collection | DOAJ |
| description | The integration of copper(I)-catalyzed three-component coupling with gold(I)-mediated 6-endo cyclization streamlines the rapid and modular assembly of the substructure of bis-tetrahydroisoquinoline (THIQ) alkaloids. The design of the key synthetic intermediate bearing a 2,3-diaminobenzofuran moiety allows both gold(I)-mediated regiocontrolled 6-endo hydroamination and temporary protection of nitrile and phenolic hydroxy groups. The synthetic strategy enabled the efficient synthesis of the substructure of saframycins bearing isoquinoline and THIQ units in just four steps from the modular assembly of the three components. We also found the unexpected involvement of a fluorescent intermediate in the cascade synthetic process. |
| format | Article |
| id | doaj-art-f7beb17858f541b086e41d0e5b504067 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-f7beb17858f541b086e41d0e5b5040672025-02-03T09:10:17ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-01-0121122623310.3762/bjoc.21.141860-5397-21-14Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclizationAsahi Kanno0Ryo Tanifuji1Satoshi Yoshida2Sota Sato3Saori Maki-Yonekura4Kiyofumi Takaba5Jungmin Kang6Kensuke Tono7Koji Yonekura8Hiroki Oguri9Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan Department of Applied Chemistry, School of Engineering, The University of Tokyo, FS CREATION, Mitsui LINK Lab Kashiwanoha 1, 6-6-2 Kashiwanoha, Kashiwa, Chiba, 227-0882, Japan Department of Applied Chemistry, School of Engineering, The University of Tokyo, FS CREATION, Mitsui LINK Lab Kashiwanoha 1, 6-6-2 Kashiwanoha, Kashiwa, Chiba, 227-0882, Japan RIKEN SPring-8 Center, 1-1-1 Kouto, Sayo, Hyogo 679-5148, Japan RIKEN SPring-8 Center, 1-1-1 Kouto, Sayo, Hyogo 679-5148, Japan RIKEN SPring-8 Center, 1-1-1 Kouto, Sayo, Hyogo 679-5148, Japan RIKEN SPring-8 Center, 1-1-1 Kouto, Sayo, Hyogo 679-5148, Japan RIKEN SPring-8 Center, 1-1-1 Kouto, Sayo, Hyogo 679-5148, Japan Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan The integration of copper(I)-catalyzed three-component coupling with gold(I)-mediated 6-endo cyclization streamlines the rapid and modular assembly of the substructure of bis-tetrahydroisoquinoline (THIQ) alkaloids. The design of the key synthetic intermediate bearing a 2,3-diaminobenzofuran moiety allows both gold(I)-mediated regiocontrolled 6-endo hydroamination and temporary protection of nitrile and phenolic hydroxy groups. The synthetic strategy enabled the efficient synthesis of the substructure of saframycins bearing isoquinoline and THIQ units in just four steps from the modular assembly of the three components. We also found the unexpected involvement of a fluorescent intermediate in the cascade synthetic process.https://doi.org/10.3762/bjoc.21.14cascade reactionscopper-catalyzed three-component couplinggold-mediated 6-endo hydroaminationtandem cyclizationstetrahydroisoquinoline alkaloids |
| spellingShingle | Asahi Kanno Ryo Tanifuji Satoshi Yoshida Sota Sato Saori Maki-Yonekura Kiyofumi Takaba Jungmin Kang Kensuke Tono Koji Yonekura Hiroki Oguri Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization Beilstein Journal of Organic Chemistry cascade reactions copper-catalyzed three-component coupling gold-mediated 6-endo hydroamination tandem cyclizations tetrahydroisoquinoline alkaloids |
| title | Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization |
| title_full | Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization |
| title_fullStr | Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization |
| title_full_unstemmed | Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization |
| title_short | Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization |
| title_sort | streamlined modular synthesis of saframycin substructure via copper catalyzed three component assembly and gold promoted 6 endo cyclization |
| topic | cascade reactions copper-catalyzed three-component coupling gold-mediated 6-endo hydroamination tandem cyclizations tetrahydroisoquinoline alkaloids |
| url | https://doi.org/10.3762/bjoc.21.14 |
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