Routes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols A and B
<p>A short route from dihydrocarvone is described, which led to the tetracarbocyclic core common to artatrovirenol A and B and daphnenoid A. A variant of this route afforded guaia-4,6-dien-3-one (from <em>Enterospermum madagascarensis</em>) and its epimer. From 2-(2-oxoeth...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2024
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| _version_ | 1797113246115692544 |
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| author | Zong, J Christensen, KE Robertson, J |
| author_facet | Zong, J Christensen, KE Robertson, J |
| author_sort | Zong, J |
| collection | OXFORD |
| description | <p>A short route from dihydrocarvone is described, which led to the tetracarbocyclic core common to artatrovirenol A and B and daphnenoid A. A variant of this route afforded guaia-4,6-dien-3-one (from <em>Enterospermum madagascarensis</em>) and its epimer. From 2-(2-oxoethyl)furan, a 15-step sequence then delivered the complete carbon skeleton and all functionality necessary for daphnenoid A. Key steps in the route include diastereoselective intramolecular oxidopyrylium cycloaddition, oxa-bridge cleavage under “push–pull” conditions, and intramolecular Diels–Alder cycloaddition.</p> |
| first_indexed | 2024-03-07T08:26:17Z |
| format | Journal article |
| id | oxford-uuid:7dd0dc44-779a-47e9-848a-f25c3a0c9d91 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-04-23T08:25:46Z |
| publishDate | 2024 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:7dd0dc44-779a-47e9-848a-f25c3a0c9d912024-04-15T07:14:42ZRoutes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols A and BJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:7dd0dc44-779a-47e9-848a-f25c3a0c9d91EnglishSymplectic ElementsAmerican Chemical Society2024Zong, JChristensen, KERobertson, J<p>A short route from dihydrocarvone is described, which led to the tetracarbocyclic core common to artatrovirenol A and B and daphnenoid A. A variant of this route afforded guaia-4,6-dien-3-one (from <em>Enterospermum madagascarensis</em>) and its epimer. From 2-(2-oxoethyl)furan, a 15-step sequence then delivered the complete carbon skeleton and all functionality necessary for daphnenoid A. Key steps in the route include diastereoselective intramolecular oxidopyrylium cycloaddition, oxa-bridge cleavage under “push–pull” conditions, and intramolecular Diels–Alder cycloaddition.</p> |
| spellingShingle | Zong, J Christensen, KE Robertson, J Routes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols A and B |
| title | Routes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols A and B |
| title_full | Routes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols A and B |
| title_fullStr | Routes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols A and B |
| title_full_unstemmed | Routes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols A and B |
| title_short | Routes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols A and B |
| title_sort | routes to advanced intermediates in the synthesis of tetracarbocyclic sesquiterpenoids daphnenoid a and artatrovirenols a and b |
| work_keys_str_mv | AT zongj routestoadvancedintermediatesinthesynthesisoftetracarbocyclicsesquiterpenoidsdaphnenoidaandartatrovirenolsaandb AT christensenke routestoadvancedintermediatesinthesynthesisoftetracarbocyclicsesquiterpenoidsdaphnenoidaandartatrovirenolsaandb AT robertsonj routestoadvancedintermediatesinthesynthesisoftetracarbocyclicsesquiterpenoidsdaphnenoidaandartatrovirenolsaandb |