Structure and Computational Basis for Backbone Rearrangement in Marine Oxasqualenoids
Six novel oxasqualenoids (polyether triterpenes) were isolated from the red alga Laurencia viridis. Laurokanols A–E (1–5) comprise an unreported tricyclic core with a [6,6]-spiroketal system. Yucatecone (6) shows a biogenetically intriguing epimerization at C14. Quantum mechanical calculations were used to corroborate their structures and to explain key steps involved in the biogenetic mechanisms proposed for the formation of oxasqualenoids.
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| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Language: | English |
| Published: |
American Chemical Society
2020-12-28
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| Subjects: | Free energy, Reaction mechanisms, Chemical structure, Molecular structure, Chemical calculations, |
| Online Access: | http://hdl.handle.net/10261/226918 http://dx.doi.org/10.13039/100000001 http://dx.doi.org/10.13039/501100003141 http://dx.doi.org/10.13039/100012000 http://dx.doi.org/10.13039/501100004837 |
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| Summary: | Six novel oxasqualenoids (polyether triterpenes) were isolated from the red alga Laurencia viridis. Laurokanols A–E (1–5) comprise an unreported tricyclic core with a [6,6]-spiroketal system. Yucatecone (6) shows a biogenetically intriguing epimerization at C14. Quantum mechanical calculations were used to corroborate their structures and to explain key steps involved in the biogenetic mechanisms proposed for the formation of oxasqualenoids. |
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