Bioinspired asymmetric synthesis of (-)-gymnothelignan v
© 2018 American Chemical Society. A bioinspired asymmetric total synthesis of a structurally unique subtype of lignan, namely, (-)-gymnothelignan V, was achieved. The key synthetic sequences involved reduction of the eupomatilone skeleton leading to (-)-gymnothelignan J followed by the formation of...
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th-mahidol.455002019-08-23T17:50:43Z Bioinspired asymmetric synthesis of (-)-gymnothelignan v Darunee Soorukram Manat Pohmakotr Chutima Kuhakarn Vichai Reutrakul Mahidol University Chemistry © 2018 American Chemical Society. A bioinspired asymmetric total synthesis of a structurally unique subtype of lignan, namely, (-)-gymnothelignan V, was achieved. The key synthetic sequences involved reduction of the eupomatilone skeleton leading to (-)-gymnothelignan J followed by the formation of the corresponding oxocarbenium ion and stereoselective intramolecular Friedel-Crafts reaction. Our synthetic approach provides the information to support the plausible biosynthetic pathway of this structurally unusual lignan. On a similar basis, other structurally related natural and non-natural gymnothelignans including (-)-gymnothelignan D, 6,9-bis-epi-gymnothelignan V, and 5-epi-gymnothelignans D and J were readily prepared. 2019-08-23T10:50:43Z 2019-08-23T10:50:43Z 2018-04-06 Article Journal of Organic Chemistry. Vol.83, No.7 (2018), 4173-4179 10.1021/acs.joc.8b00164 15206904 00223263 2-s2.0-85045127239 https://repository.li.mahidol.ac.th/handle/123456789/45500 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85045127239&origin=inward |
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Chemistry Darunee Soorukram Manat Pohmakotr Chutima Kuhakarn Vichai Reutrakul Bioinspired asymmetric synthesis of (-)-gymnothelignan v |
| description |
© 2018 American Chemical Society. A bioinspired asymmetric total synthesis of a structurally unique subtype of lignan, namely, (-)-gymnothelignan V, was achieved. The key synthetic sequences involved reduction of the eupomatilone skeleton leading to (-)-gymnothelignan J followed by the formation of the corresponding oxocarbenium ion and stereoselective intramolecular Friedel-Crafts reaction. Our synthetic approach provides the information to support the plausible biosynthetic pathway of this structurally unusual lignan. On a similar basis, other structurally related natural and non-natural gymnothelignans including (-)-gymnothelignan D, 6,9-bis-epi-gymnothelignan V, and 5-epi-gymnothelignans D and J were readily prepared. |
| author2 |
Mahidol University |
| author_facet |
Mahidol University Darunee Soorukram Manat Pohmakotr Chutima Kuhakarn Vichai Reutrakul |
| format |
Article |
| author |
Darunee Soorukram Manat Pohmakotr Chutima Kuhakarn Vichai Reutrakul |
| author_sort |
Darunee Soorukram |
| title |
Bioinspired asymmetric synthesis of (-)-gymnothelignan v |
| title_short |
Bioinspired asymmetric synthesis of (-)-gymnothelignan v |
| title_full |
Bioinspired asymmetric synthesis of (-)-gymnothelignan v |
| title_fullStr |
Bioinspired asymmetric synthesis of (-)-gymnothelignan v |
| title_full_unstemmed |
Bioinspired asymmetric synthesis of (-)-gymnothelignan v |
| title_sort |
bioinspired asymmetric synthesis of (-)-gymnothelignan v |
| publishDate |
2019 |
| url |
https://repository.li.mahidol.ac.th/handle/123456789/45500 |
| _version_ |
1763493152277135360 |