Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step
Marine meroterpenoids have attracted a great deal of attention from synthetic research groups due to their attractive and varied biological activities and their unique and diverse structures. In most cases, however, further biological studies have been severely limited mainly to the scarcity of natu...
| Main Authors: | , , |
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| Format: | info:eu-repo/semantics/article |
| Language: | English |
| Published: |
MDPI
2023
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| Subjects: | |
| Online Access: | http://hdl.handle.net/10835/14348 |
| _version_ | 1789406678945366016 |
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| author | Rosales Martínez, Antonio Rodríguez-Maecker, Román Nicolay Rodríguez García, Ignacio |
| author_facet | Rosales Martínez, Antonio Rodríguez-Maecker, Román Nicolay Rodríguez García, Ignacio |
| author_sort | Rosales Martínez, Antonio |
| collection | DSpace |
| description | Marine meroterpenoids have attracted a great deal of attention from synthetic research groups due to their attractive and varied biological activities and their unique and diverse structures. In most cases, however, further biological studies have been severely limited mainly to the scarcity of natural supply and because almost none of the reported syntheses methods has enabled unified access for a large number of marine meroterpenoids with aureane and avarane skeletons. Based on our previous publications and the study of recent manuscripts on marine meroterpenoids, we have conceived a unified strategy for these fascinating marine compounds with aureane or avarane skeletons using available drimane compounds as starting materials. The key step is a biosynthetic sequence of 1,2-hydride and methyl shifts. This strategy is of great synthetic value to access marine meroterpenoids through easy chemical synthetic procedures. Finally, several retrosynthetic proposals are made for the future synthesis of several members of this class of meroterpenoids, focused on consolidating these 1,2-rearrangements as a versatile and unified strategy that could be widely used in the preparation of these marine meroterpenoids. |
| format | info:eu-repo/semantics/article |
| id | oai:repositorio.ual.es:10835-14348 |
| institution | Universidad de Cuenca |
| language | English |
| publishDate | 2023 |
| publisher | MDPI |
| record_format | dspace |
| spelling | oai:repositorio.ual.es:10835-143482023-04-12T19:47:58Z Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step Rosales Martínez, Antonio Rodríguez-Maecker, Román Nicolay Rodríguez García, Ignacio marine natural products meroterpenoids rearrangements synthetic strategies Marine meroterpenoids have attracted a great deal of attention from synthetic research groups due to their attractive and varied biological activities and their unique and diverse structures. In most cases, however, further biological studies have been severely limited mainly to the scarcity of natural supply and because almost none of the reported syntheses methods has enabled unified access for a large number of marine meroterpenoids with aureane and avarane skeletons. Based on our previous publications and the study of recent manuscripts on marine meroterpenoids, we have conceived a unified strategy for these fascinating marine compounds with aureane or avarane skeletons using available drimane compounds as starting materials. The key step is a biosynthetic sequence of 1,2-hydride and methyl shifts. This strategy is of great synthetic value to access marine meroterpenoids through easy chemical synthetic procedures. Finally, several retrosynthetic proposals are made for the future synthesis of several members of this class of meroterpenoids, focused on consolidating these 1,2-rearrangements as a versatile and unified strategy that could be widely used in the preparation of these marine meroterpenoids. 2023-02-23T15:18:27Z 2023-02-23T15:18:27Z 2023-02-10 info:eu-repo/semantics/article 1660-3397 http://hdl.handle.net/10835/14348 10.3390/md21020118 en https://www.mdpi.com/1660-3397/21/2/118 Attribution-NonCommercial-NoDerivatives 4.0 Internacional http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess MDPI |
| spellingShingle | marine natural products meroterpenoids rearrangements synthetic strategies Rosales Martínez, Antonio Rodríguez-Maecker, Román Nicolay Rodríguez García, Ignacio Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step |
| title | Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step |
| title_full | Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step |
| title_fullStr | Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step |
| title_full_unstemmed | Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step |
| title_short | Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step |
| title_sort | unifying the synthesis of a whole family of marine meroterpenoids through a biosynthetically inspired sequence of 1,2-hydride and methyl shifts as key step |
| topic | marine natural products meroterpenoids rearrangements synthetic strategies |
| url | http://hdl.handle.net/10835/14348 |
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