Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products
Marine polycyclic ether natural products have gained significant interest from the chemical community due to their impressively huge molecular architecture and diverse biological functions. The structure assignment of this class of extraordinarily complex natural products has mainly relied on NMR sp...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-04-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/19/5/257 |
| _version_ | 1797535693793132544 |
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| author | Haruhiko Fuwa |
| author_facet | Haruhiko Fuwa |
| author_sort | Haruhiko Fuwa |
| collection | DOAJ |
| description | Marine polycyclic ether natural products have gained significant interest from the chemical community due to their impressively huge molecular architecture and diverse biological functions. The structure assignment of this class of extraordinarily complex natural products has mainly relied on NMR spectroscopic analysis. However, NMR spectroscopic analysis has its own limitations, including configurational assignment of stereogenic centers within conformationally flexible systems. Chemical shift deviation analysis of synthetic model compounds is a reliable means to assign the relative configuration of “difficult” stereogenic centers. The complete configurational assignment must be ultimately established through total synthesis. The aim of this review is to summarize the indispensable role of organic synthesis in stereochemical assignment of marine polycyclic ethers. |
| first_indexed | 2024-03-10T11:49:01Z |
| format | Article |
| id | doaj.art-450b016f5f6d4db88134ee29eab900dc |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T11:49:01Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-450b016f5f6d4db88134ee29eab900dc2023-11-21T17:50:34ZengMDPI AGMarine Drugs1660-33972021-04-0119525710.3390/md19050257Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural ProductsHaruhiko Fuwa0Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, JapanMarine polycyclic ether natural products have gained significant interest from the chemical community due to their impressively huge molecular architecture and diverse biological functions. The structure assignment of this class of extraordinarily complex natural products has mainly relied on NMR spectroscopic analysis. However, NMR spectroscopic analysis has its own limitations, including configurational assignment of stereogenic centers within conformationally flexible systems. Chemical shift deviation analysis of synthetic model compounds is a reliable means to assign the relative configuration of “difficult” stereogenic centers. The complete configurational assignment must be ultimately established through total synthesis. The aim of this review is to summarize the indispensable role of organic synthesis in stereochemical assignment of marine polycyclic ethers.https://www.mdpi.com/1660-3397/19/5/257polycyclic ethersdinoflagellatessecondary metabolitesneurotoxinstotal synthesispartial synthesis |
| spellingShingle | Haruhiko Fuwa Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products Marine Drugs polycyclic ethers dinoflagellates secondary metabolites neurotoxins total synthesis partial synthesis |
| title | Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products |
| title_full | Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products |
| title_fullStr | Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products |
| title_full_unstemmed | Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products |
| title_short | Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products |
| title_sort | synthesis driven stereochemical assignment of marine polycyclic ether natural products |
| topic | polycyclic ethers dinoflagellates secondary metabolites neurotoxins total synthesis partial synthesis |
| url | https://www.mdpi.com/1660-3397/19/5/257 |
| work_keys_str_mv | AT haruhikofuwa synthesisdrivenstereochemicalassignmentofmarinepolycyclicethernaturalproducts |