Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement
The substituted furan carboxaldehyde 15 was converted into enone 20 via a stereoselective intramolecular pyrylium ylide-alkene cyclization. Subsequent elaboration of 20 into the triflate 23, followed by solvolysis in acidic trifluoroethanol resulted in quantitative rearrangement to the taxane B/C co...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
1996
|
| _version_ | 1826273640873721856 |
|---|---|
| author | Magnus, P Diorazio, L Donohoe, T Giles, M Pye, P Tarrant, J Thom, S |
| author_facet | Magnus, P Diorazio, L Donohoe, T Giles, M Pye, P Tarrant, J Thom, S |
| author_sort | Magnus, P |
| collection | OXFORD |
| description | The substituted furan carboxaldehyde 15 was converted into enone 20 via a stereoselective intramolecular pyrylium ylide-alkene cyclization. Subsequent elaboration of 20 into the triflate 23, followed by solvolysis in acidic trifluoroethanol resulted in quantitative rearrangement to the taxane B/C core 24. At a higher oxidation level 27 was ring expanded to give 28. The ring expanson strategy could also be initiated by β-elimination of the 3α,10α-oxido bridge. Treatment of 50 with MeOH at reflux gave 52. Similar transformations in the 7-oxy series resulted in ring B expansion of 67 to give 68, and 75 to give 76. |
| first_indexed | 2024-03-06T22:31:18Z |
| format | Journal article |
| id | oxford-uuid:585f10a4-e713-4109-aaf1-72d6c821caa7 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:31:18Z |
| publishDate | 1996 |
| record_format | dspace |
| spelling | oxford-uuid:585f10a4-e713-4109-aaf1-72d6c821caa72022-03-26T17:02:59ZTaxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangementJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:585f10a4-e713-4109-aaf1-72d6c821caa7EnglishSymplectic Elements at Oxford1996Magnus, PDiorazio, LDonohoe, TGiles, MPye, PTarrant, JThom, SThe substituted furan carboxaldehyde 15 was converted into enone 20 via a stereoselective intramolecular pyrylium ylide-alkene cyclization. Subsequent elaboration of 20 into the triflate 23, followed by solvolysis in acidic trifluoroethanol resulted in quantitative rearrangement to the taxane B/C core 24. At a higher oxidation level 27 was ring expanded to give 28. The ring expanson strategy could also be initiated by β-elimination of the 3α,10α-oxido bridge. Treatment of 50 with MeOH at reflux gave 52. Similar transformations in the 7-oxy series resulted in ring B expansion of 67 to give 68, and 75 to give 76. |
| spellingShingle | Magnus, P Diorazio, L Donohoe, T Giles, M Pye, P Tarrant, J Thom, S Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement |
| title | Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement |
| title_full | Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement |
| title_fullStr | Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement |
| title_full_unstemmed | Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement |
| title_short | Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement |
| title_sort | taxane diterpenes 3 formation of the eight membered b ring by semi pinacol rearrangement |
| work_keys_str_mv | AT magnusp taxanediterpenes3formationoftheeightmemberedbringbysemipinacolrearrangement AT dioraziol taxanediterpenes3formationoftheeightmemberedbringbysemipinacolrearrangement AT donohoet taxanediterpenes3formationoftheeightmemberedbringbysemipinacolrearrangement AT gilesm taxanediterpenes3formationoftheeightmemberedbringbysemipinacolrearrangement AT pyep taxanediterpenes3formationoftheeightmemberedbringbysemipinacolrearrangement AT tarrantj taxanediterpenes3formationoftheeightmemberedbringbysemipinacolrearrangement AT thoms taxanediterpenes3formationoftheeightmemberedbringbysemipinacolrearrangement |