A concise synthesis of the octalactins.
The total synthesis of octalactins A and B has been achieved in 15 steps (longest linear sequence) and 10% overall yield from commercially available materials. Key steps include the Paterson-Aldol reaction for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearran...
| Main Authors: | , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2004
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| _version_ | 1826306123258396672 |
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| author | O'Sullivan, P Buhr, W Fuhry, M Harrison, JR Davies, J Feeder, N Marshall, DR Burton, J Holmes, AB |
| author_facet | O'Sullivan, P Buhr, W Fuhry, M Harrison, JR Davies, J Feeder, N Marshall, DR Burton, J Holmes, AB |
| author_sort | O'Sullivan, P |
| collection | OXFORD |
| description | The total synthesis of octalactins A and B has been achieved in 15 steps (longest linear sequence) and 10% overall yield from commercially available materials. Key steps include the Paterson-Aldol reaction for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearrangement of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring lactone 47, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone. |
| first_indexed | 2024-03-07T06:43:10Z |
| format | Journal article |
| id | oxford-uuid:f9fc0eb7-bc0a-44bd-9c83-cbcf7e1d8df2 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:43:10Z |
| publishDate | 2004 |
| record_format | dspace |
| spelling | oxford-uuid:f9fc0eb7-bc0a-44bd-9c83-cbcf7e1d8df22022-03-27T13:02:11ZA concise synthesis of the octalactins.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:f9fc0eb7-bc0a-44bd-9c83-cbcf7e1d8df2EnglishSymplectic Elements at Oxford2004O'Sullivan, PBuhr, WFuhry, MHarrison, JRDavies, JFeeder, NMarshall, DRBurton, JHolmes, ABThe total synthesis of octalactins A and B has been achieved in 15 steps (longest linear sequence) and 10% overall yield from commercially available materials. Key steps include the Paterson-Aldol reaction for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearrangement of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring lactone 47, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone. |
| spellingShingle | O'Sullivan, P Buhr, W Fuhry, M Harrison, JR Davies, J Feeder, N Marshall, DR Burton, J Holmes, AB A concise synthesis of the octalactins. |
| title | A concise synthesis of the octalactins. |
| title_full | A concise synthesis of the octalactins. |
| title_fullStr | A concise synthesis of the octalactins. |
| title_full_unstemmed | A concise synthesis of the octalactins. |
| title_short | A concise synthesis of the octalactins. |
| title_sort | concise synthesis of the octalactins |
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