Asymmetric total synthesis of (−)-(3R)-inthomycin C
A short (10 step) and efficient (15% overall yield) synthesis of the natural product (−)-(3R)-inthomycin C is reported. The key steps comprise three C–C bond-forming reactions: (i) a vinylogous Mukaiyama aldol, (ii) an olefin cross-metathesis reaction, and (iii) an asymmetric Mukaiyama–Kiyooka aldol...
| Автори: | , , , , , |
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| Формат: | Journal article |
| Опубліковано: |
American Chemical Society
2018
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| _version_ | 1826297233025269760 |
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| author | Balcells, S Haughey, M Walker, J Josa-Cullere, L Towers, C Donohoe, T |
| author_facet | Balcells, S Haughey, M Walker, J Josa-Cullere, L Towers, C Donohoe, T |
| author_sort | Balcells, S |
| collection | OXFORD |
| description | A short (10 step) and efficient (15% overall yield) synthesis of the natural product (−)-(3R)-inthomycin C is reported. The key steps comprise three C–C bond-forming reactions: (i) a vinylogous Mukaiyama aldol, (ii) an olefin cross-metathesis reaction, and (iii) an asymmetric Mukaiyama–Kiyooka aldol. This route is notable for its brevity and has the advantage of lacking stoichiometric tin-promoted cross-coupling reactions present in previous approaches. Initial investigations on the biological activity of (−)-(3R)-inthomycin C and structural analogues on human cancer cell lines are also described for the first time. |
| first_indexed | 2024-03-07T04:28:27Z |
| format | Journal article |
| id | oxford-uuid:cd7995aa-ec45-40df-bf0f-d6033e8f35ee |
| institution | University of Oxford |
| last_indexed | 2024-03-07T04:28:27Z |
| publishDate | 2018 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:cd7995aa-ec45-40df-bf0f-d6033e8f35ee2022-03-27T07:28:57ZAsymmetric total synthesis of (−)-(3R)-inthomycin CJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:cd7995aa-ec45-40df-bf0f-d6033e8f35eeSymplectic Elements at OxfordAmerican Chemical Society2018Balcells, SHaughey, MWalker, JJosa-Cullere, LTowers, CDonohoe, TA short (10 step) and efficient (15% overall yield) synthesis of the natural product (−)-(3R)-inthomycin C is reported. The key steps comprise three C–C bond-forming reactions: (i) a vinylogous Mukaiyama aldol, (ii) an olefin cross-metathesis reaction, and (iii) an asymmetric Mukaiyama–Kiyooka aldol. This route is notable for its brevity and has the advantage of lacking stoichiometric tin-promoted cross-coupling reactions present in previous approaches. Initial investigations on the biological activity of (−)-(3R)-inthomycin C and structural analogues on human cancer cell lines are also described for the first time. |
| spellingShingle | Balcells, S Haughey, M Walker, J Josa-Cullere, L Towers, C Donohoe, T Asymmetric total synthesis of (−)-(3R)-inthomycin C |
| title | Asymmetric total synthesis of (−)-(3R)-inthomycin C |
| title_full | Asymmetric total synthesis of (−)-(3R)-inthomycin C |
| title_fullStr | Asymmetric total synthesis of (−)-(3R)-inthomycin C |
| title_full_unstemmed | Asymmetric total synthesis of (−)-(3R)-inthomycin C |
| title_short | Asymmetric total synthesis of (−)-(3R)-inthomycin C |
| title_sort | asymmetric total synthesis of 3r inthomycin c |
| work_keys_str_mv | AT balcellss asymmetrictotalsynthesisof3rinthomycinc AT haugheym asymmetrictotalsynthesisof3rinthomycinc AT walkerj asymmetrictotalsynthesisof3rinthomycinc AT josacullerel asymmetrictotalsynthesisof3rinthomycinc AT towersc asymmetrictotalsynthesisof3rinthomycinc AT donohoet asymmetrictotalsynthesisof3rinthomycinc |