Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D.
Two routes are described for the synthesis of the sawaranospirolides, stereoisomeric spirolactone ascorbigenins isolated from Chamaecyparis pisifera. Trapping of the keto enal formed by oxidation of a functionalised 2-(4-hydroxybutyl)furan affords a potential butenolide spiroacetal precursor to sawa...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
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2010
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| _version_ | 1797068410183483392 |
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| author | Robertson, J Chovatia, P Fowler, T Withey, J Woollaston, D |
| author_facet | Robertson, J Chovatia, P Fowler, T Withey, J Woollaston, D |
| author_sort | Robertson, J |
| collection | OXFORD |
| description | Two routes are described for the synthesis of the sawaranospirolides, stereoisomeric spirolactone ascorbigenins isolated from Chamaecyparis pisifera. Trapping of the keto enal formed by oxidation of a functionalised 2-(4-hydroxybutyl)furan affords a potential butenolide spiroacetal precursor to sawaranospirolides A and C. Alternatively, epoxidation of protected 3-(dihydropyran-2-yl)-3-arylpropanoic acids results in spirolactonisation to generate ent-sawaranospirolide C; a related acid-mediated spirocyclisation gave access to ent-sawaranospirolide D. |
| first_indexed | 2024-03-06T22:10:23Z |
| format | Journal article |
| id | oxford-uuid:519a19b2-9d71-4236-9ea6-4422d5d22e07 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:10:23Z |
| publishDate | 2010 |
| record_format | dspace |
| spelling | oxford-uuid:519a19b2-9d71-4236-9ea6-4422d5d22e072022-03-26T16:20:30ZOxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:519a19b2-9d71-4236-9ea6-4422d5d22e07EnglishSymplectic Elements at Oxford2010Robertson, JChovatia, PFowler, TWithey, JWoollaston, DTwo routes are described for the synthesis of the sawaranospirolides, stereoisomeric spirolactone ascorbigenins isolated from Chamaecyparis pisifera. Trapping of the keto enal formed by oxidation of a functionalised 2-(4-hydroxybutyl)furan affords a potential butenolide spiroacetal precursor to sawaranospirolides A and C. Alternatively, epoxidation of protected 3-(dihydropyran-2-yl)-3-arylpropanoic acids results in spirolactonisation to generate ent-sawaranospirolide C; a related acid-mediated spirocyclisation gave access to ent-sawaranospirolide D. |
| spellingShingle | Robertson, J Chovatia, P Fowler, T Withey, J Woollaston, D Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D. |
| title | Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D. |
| title_full | Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D. |
| title_fullStr | Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D. |
| title_full_unstemmed | Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D. |
| title_short | Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D. |
| title_sort | oxidative spirocyclisation routes towards the sawaranospirolides synthesis of ent sawaranospirolides c and d |
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