Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile
The Taxol core was prepared in five steps via a key copper-catalyzed asymmetric conjugate addition trapping sequence. The use of a bromodiene-derived alkylzirconium nucleophile followed by trapping with POCl3/DMF gave a highly functionalized intermediate featuring a quaternary center in 69% yield wi...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2020
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| _version_ | 1826307270471843840 |
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| author | Wang, JYJ Fletcher, S |
| author_facet | Wang, JYJ Fletcher, S |
| author_sort | Wang, JYJ |
| collection | OXFORD |
| description | The Taxol core was prepared in five steps via a key copper-catalyzed asymmetric conjugate addition trapping sequence. The use of a bromodiene-derived alkylzirconium nucleophile followed by trapping with POCl3/DMF gave a highly functionalized intermediate featuring a quaternary center in 69% yield with 92% ee. After 1,2-addition, Suzuki–Miyaura cross-coupling, allylic oxidation, and a type II intramolecular Diels–Alder reaction, the taxol core was obtained in 11% overall yield with 92% ee. |
| first_indexed | 2024-03-07T07:00:24Z |
| format | Journal article |
| id | oxford-uuid:ff8b4ba1-c6f5-49b7-854a-d6c1be61cdef |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:00:24Z |
| publishDate | 2020 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:ff8b4ba1-c6f5-49b7-854a-d6c1be61cdef2022-03-27T13:45:48ZSynthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium NucleophileJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ff8b4ba1-c6f5-49b7-854a-d6c1be61cdefEnglishSymplectic ElementsAmerican Chemical Society2020Wang, JYJFletcher, SThe Taxol core was prepared in five steps via a key copper-catalyzed asymmetric conjugate addition trapping sequence. The use of a bromodiene-derived alkylzirconium nucleophile followed by trapping with POCl3/DMF gave a highly functionalized intermediate featuring a quaternary center in 69% yield with 92% ee. After 1,2-addition, Suzuki–Miyaura cross-coupling, allylic oxidation, and a type II intramolecular Diels–Alder reaction, the taxol core was obtained in 11% overall yield with 92% ee. |
| spellingShingle | Wang, JYJ Fletcher, S Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile |
| title | Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile |
| title_full | Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile |
| title_fullStr | Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile |
| title_full_unstemmed | Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile |
| title_short | Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile |
| title_sort | synthesis of the taxol core via catalytic asymmetric 1 4 addition of an alkylzirconium nucleophile |
| work_keys_str_mv | AT wangjyj synthesisofthetaxolcoreviacatalyticasymmetric14additionofanalkylzirconiumnucleophile AT fletchers synthesisofthetaxolcoreviacatalyticasymmetric14additionofanalkylzirconiumnucleophile |