Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl
Heating a 2,5-furanocyclic (2-azidoethyl)allene initiates a cascade reaction comprising azide–allene cycloaddition, loss of nitrogen, and azatrimethylenemethane (ATMM) diyl–furan transannular (4+3)-cycloaddition. The major product of this reaction contains the pentacyclic core common to guanacastepe...
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| Format: | Journal article |
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American Chemical Society
2017
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| _version_ | 1797075770184564736 |
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| author | Zhurakovskyi, O Ellis, S Thompson, A Robertson, J |
| author_facet | Zhurakovskyi, O Ellis, S Thompson, A Robertson, J |
| author_sort | Zhurakovskyi, O |
| collection | OXFORD |
| description | Heating a 2,5-furanocyclic (2-azidoethyl)allene initiates a cascade reaction comprising azide–allene cycloaddition, loss of nitrogen, and azatrimethylenemethane (ATMM) diyl–furan transannular (4+3)-cycloaddition. The major product of this reaction contains the pentacyclic core common to guanacastepenes D and H, and radianspenes J–L; in addition, the central oxabridged cycloheptene ring, flanked by two carbocyclic rings, is structurally related to the ABC-ring system found in the cortistatins. This is the first reported synthetic application of a ‘free’ (non-conjugated) ATMM. The cyclization precursors were prepared via the first reported examples of the Ireland–Claisen rearrangement of an ethynyl lactone. |
| first_indexed | 2024-03-06T23:54:54Z |
| format | Journal article |
| id | oxford-uuid:73e171c1-1fb4-4aa1-a26e-4544f0bb4b03 |
| institution | University of Oxford |
| last_indexed | 2024-03-06T23:54:54Z |
| publishDate | 2017 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:73e171c1-1fb4-4aa1-a26e-4544f0bb4b032022-03-26T19:59:10ZAccess to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diylJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:73e171c1-1fb4-4aa1-a26e-4544f0bb4b03Symplectic Elements at OxfordAmerican Chemical Society2017Zhurakovskyi, OEllis, SThompson, ARobertson, JHeating a 2,5-furanocyclic (2-azidoethyl)allene initiates a cascade reaction comprising azide–allene cycloaddition, loss of nitrogen, and azatrimethylenemethane (ATMM) diyl–furan transannular (4+3)-cycloaddition. The major product of this reaction contains the pentacyclic core common to guanacastepenes D and H, and radianspenes J–L; in addition, the central oxabridged cycloheptene ring, flanked by two carbocyclic rings, is structurally related to the ABC-ring system found in the cortistatins. This is the first reported synthetic application of a ‘free’ (non-conjugated) ATMM. The cyclization precursors were prepared via the first reported examples of the Ireland–Claisen rearrangement of an ethynyl lactone. |
| spellingShingle | Zhurakovskyi, O Ellis, S Thompson, A Robertson, J Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl |
| title | Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl |
| title_full | Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl |
| title_fullStr | Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl |
| title_full_unstemmed | Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl |
| title_short | Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl |
| title_sort | access to a guanacastepene and cortistatin related skeleton via ethynyl lactone ireland claisen rearrangement and transannular 4 3 cycloaddition of an azatrimethylenemethane diyl |
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