Convergent total syntheses of (-)-rubriflordilactone B and (-)-pseudo-rubriflordilactone B
A highly convergent strategy for the synthesis of the natural product (-)-rubriflordilactone B, and the proposed structure of (-)-pseudo-rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodiu...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2019
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| _version_ | 1797052212760805376 |
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| author | Mohammad, M Chintalapudi, V Carney, J Mansfield, S Sanderson, P Christensen, K Anderson, EA |
| author_facet | Mohammad, M Chintalapudi, V Carney, J Mansfield, S Sanderson, P Christensen, K Anderson, EA |
| author_sort | Mohammad, M |
| collection | OXFORD |
| description | A highly convergent strategy for the synthesis of the natural product (-)-rubriflordilactone B, and the proposed structure of (-)-pseudo-rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium-catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo-rubriflordilactone B, and provides a robust platform for further synthetic and biological investigations. |
| first_indexed | 2024-03-06T18:29:18Z |
| format | Journal article |
| id | oxford-uuid:09170c4d-58e3-45d1-8276-b252ab84997c |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:29:18Z |
| publishDate | 2019 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:09170c4d-58e3-45d1-8276-b252ab84997c2022-03-26T09:16:24ZConvergent total syntheses of (-)-rubriflordilactone B and (-)-pseudo-rubriflordilactone BJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:09170c4d-58e3-45d1-8276-b252ab84997cEnglishSymplectic Elements at OxfordWiley2019Mohammad, MChintalapudi, VCarney, JMansfield, SSanderson, PChristensen, KAnderson, EAA highly convergent strategy for the synthesis of the natural product (-)-rubriflordilactone B, and the proposed structure of (-)-pseudo-rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium-catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo-rubriflordilactone B, and provides a robust platform for further synthetic and biological investigations. |
| spellingShingle | Mohammad, M Chintalapudi, V Carney, J Mansfield, S Sanderson, P Christensen, K Anderson, EA Convergent total syntheses of (-)-rubriflordilactone B and (-)-pseudo-rubriflordilactone B |
| title | Convergent total syntheses of (-)-rubriflordilactone B and (-)-pseudo-rubriflordilactone B |
| title_full | Convergent total syntheses of (-)-rubriflordilactone B and (-)-pseudo-rubriflordilactone B |
| title_fullStr | Convergent total syntheses of (-)-rubriflordilactone B and (-)-pseudo-rubriflordilactone B |
| title_full_unstemmed | Convergent total syntheses of (-)-rubriflordilactone B and (-)-pseudo-rubriflordilactone B |
| title_short | Convergent total syntheses of (-)-rubriflordilactone B and (-)-pseudo-rubriflordilactone B |
| title_sort | convergent total syntheses of rubriflordilactone b and pseudo rubriflordilactone b |
| work_keys_str_mv | AT mohammadm convergenttotalsynthesesofrubriflordilactonebandpseudorubriflordilactoneb AT chintalapudiv convergenttotalsynthesesofrubriflordilactonebandpseudorubriflordilactoneb AT carneyj convergenttotalsynthesesofrubriflordilactonebandpseudorubriflordilactoneb AT mansfields convergenttotalsynthesesofrubriflordilactonebandpseudorubriflordilactoneb AT sandersonp convergenttotalsynthesesofrubriflordilactonebandpseudorubriflordilactoneb AT christensenk convergenttotalsynthesesofrubriflordilactonebandpseudorubriflordilactoneb AT andersonea convergenttotalsynthesesofrubriflordilactonebandpseudorubriflordilactoneb |