Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1)
The first enantioselective total synthesis of antifungal agent Sch 38516, also known as fluvirucin B1, is described. The synthesis includes a convergent asymmetric preparation of amine 17 and acid 18, which are then united to afford diene 62. Metal-catalyzed transformations play a crucial role in th...
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| المؤلف الرئيسي: | |
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| مؤلفون آخرون: | , , , , , |
| التنسيق: | article |
| منشور في: |
1997
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| الوصول للمادة أونلاين: | http://hdl.handle.net/10725/3303 http://dx.doi.org/10.1021/ja972191k http://pubs.acs.org/doi/abs/10.1021/ja972191k |
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| _version_ | 1864513460957609984 |
|---|---|
| author | Houri, Ahmad F. |
| author2 | Xu, Zhongmin Johannes, Charles W. La, Daniel S. Cogan, Derek A. Hofilena, Glora E. Hoveyda, Amir H. |
| author2_role | author author author author author author |
| author_facet | Houri, Ahmad F. Xu, Zhongmin Johannes, Charles W. La, Daniel S. Cogan, Derek A. Hofilena, Glora E. Hoveyda, Amir H. |
| author_role | author |
| dc.creator.none.fl_str_mv | Houri, Ahmad F. Xu, Zhongmin Johannes, Charles W. La, Daniel S. Cogan, Derek A. Hofilena, Glora E. Hoveyda, Amir H. |
| dc.date.none.fl_str_mv | 1997 2016-03-08T10:46:35Z 2016-03-08T10:46:35Z 2016-05-12 |
| dc.identifier.none.fl_str_mv | 0002-7863 http://hdl.handle.net/10725/3303 http://dx.doi.org/10.1021/ja972191k Xu, Z., Johannes, C. W., Houri, A. F., La, D. S., Cogan, D. A., Hofilena, G. E., & Hoveyda, A. H. (1997). Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis. Enantioselective total synthesis of sch 38516 (fluvirucin B1). Journal of the American Chemical Society, 119(43), 10302-10316. http://pubs.acs.org/doi/abs/10.1021/ja972191k |
| dc.language.none.fl_str_mv | en |
| dc.relation.none.fl_str_mv | Journal of the American Chemical Society |
| dc.rights.*.fl_str_mv | info:eu-repo/semantics/openAccess |
| dc.title.none.fl_str_mv | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1) |
| dc.type.none.fl_str_mv | Article info:eu-repo/semantics/publishedVersion info:eu-repo/semantics/article |
| description | The first enantioselective total synthesis of antifungal agent Sch 38516, also known as fluvirucin B1, is described. The synthesis includes a convergent asymmetric preparation of amine 17 and acid 18, which are then united to afford diene 62. Metal-catalyzed transformations play a crucial role in the synthesis of the latter moiety. Of particular note are the diastereo- and enantioselective Zr-catalyzed alkylations, a tandem Ti- and Ni-catalyzed process that constitutes a hydrovinylation reaction, and a Ru-catalyzed alcohol oxidation to afford carboxylic acid 18. The requisite carbohydrate 38 is synthesized in a highly diastereo- and enantioselective fashion. Optical purity of the carbohydrate moiety arises from the use of the asymmetric dihydroxylation method of Sharpless; diastereochemical control is achieved through a selective dipolar [3 + 2] cycloaddition with a readily available amine serving as the chiral auxiliary. Union of the appropriately outfitted carbohydrate 71 and diene 62 through an efficient and diastereoselective glycosylation is followed by a remarkably efficient Mo-catalyzed macrocyclization that proceeds readily at room temperature. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | LAURepo_4c74fd2fefaf5a48b39b04652ff94884 |
| identifier_str_mv | 0002-7863 Xu, Z., Johannes, C. W., Houri, A. F., La, D. S., Cogan, D. A., Hofilena, G. E., & Hoveyda, A. H. (1997). Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis. Enantioselective total synthesis of sch 38516 (fluvirucin B1). Journal of the American Chemical Society, 119(43), 10302-10316. |
| language_invalid_str_mv | en |
| network_acronym_str | LAURepo |
| network_name_str | Lebanese American University repository |
| oai_identifier_str | oai:laur.lau.edu.lb:10725/3303 |
| publishDate | 1997 |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| spelling | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1)Houri, Ahmad F.Xu, ZhongminJohannes, Charles W.La, Daniel S.Cogan, Derek A.Hofilena, Glora E.Hoveyda, Amir H.The first enantioselective total synthesis of antifungal agent Sch 38516, also known as fluvirucin B1, is described. The synthesis includes a convergent asymmetric preparation of amine 17 and acid 18, which are then united to afford diene 62. Metal-catalyzed transformations play a crucial role in the synthesis of the latter moiety. Of particular note are the diastereo- and enantioselective Zr-catalyzed alkylations, a tandem Ti- and Ni-catalyzed process that constitutes a hydrovinylation reaction, and a Ru-catalyzed alcohol oxidation to afford carboxylic acid 18. The requisite carbohydrate 38 is synthesized in a highly diastereo- and enantioselective fashion. Optical purity of the carbohydrate moiety arises from the use of the asymmetric dihydroxylation method of Sharpless; diastereochemical control is achieved through a selective dipolar [3 + 2] cycloaddition with a readily available amine serving as the chiral auxiliary. Union of the appropriately outfitted carbohydrate 71 and diene 62 through an efficient and diastereoselective glycosylation is followed by a remarkably efficient Mo-catalyzed macrocyclization that proceeds readily at room temperature.PublishedN/A2016-03-08T10:46:35Z2016-03-08T10:46:35Z19972016-05-12Articleinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article0002-7863http://hdl.handle.net/10725/3303http://dx.doi.org/10.1021/ja972191kXu, Z., Johannes, C. W., Houri, A. F., La, D. S., Cogan, D. A., Hofilena, G. E., & Hoveyda, A. H. (1997). Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis. Enantioselective total synthesis of sch 38516 (fluvirucin B1). Journal of the American Chemical Society, 119(43), 10302-10316.http://pubs.acs.org/doi/abs/10.1021/ja972191kenJournal of the American Chemical Societyinfo:eu-repo/semantics/openAccessoai:laur.lau.edu.lb:10725/33032021-03-19T10:00:45Z |
| spellingShingle | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1) Houri, Ahmad F. |
| status_str | publishedVersion |
| title | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1) |
| title_full | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1) |
| title_fullStr | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1) |
| title_full_unstemmed | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1) |
| title_short | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1) |
| title_sort | Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1) |
| url | http://hdl.handle.net/10725/3303 http://dx.doi.org/10.1021/ja972191k http://pubs.acs.org/doi/abs/10.1021/ja972191k |