Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition
The chemo- and enantioselective reduction of ethyl 4-chloroacetoacetate and the diastereoselective conjugate addition of enantiopure lithium N-benzyl-N-(α-methylbenzyl)amide to an α,β-unsaturated ester have been used as the key steps in the total asymmetric syntheses of (+)-negamycin (in 13 steps an...
| Hauptverfasser: | , , , |
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| Format: | Journal article |
| Sprache: | English |
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2011
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| _version_ | 1826277218142126080 |
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| author | Davies, S Ichihara, O Roberts, P Thomson, J |
| author_facet | Davies, S Ichihara, O Roberts, P Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The chemo- and enantioselective reduction of ethyl 4-chloroacetoacetate and the diastereoselective conjugate addition of enantiopure lithium N-benzyl-N-(α-methylbenzyl)amide to an α,β-unsaturated ester have been used as the key steps in the total asymmetric syntheses of (+)-negamycin (in 13 steps and 24% overall yield), (+)-3-epi-negamycin (in 13 steps and 10% overall yield) and sperabillin C (in 17 steps and 13% overall yield) from commercially available starting materials. © 2010 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-06T23:25:36Z |
| format | Journal article |
| id | oxford-uuid:6a432f04-834c-4e86-9583-e3e6a754a75c |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T23:25:36Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:6a432f04-834c-4e86-9583-e3e6a754a75c2022-03-26T18:56:18ZAsymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate additionJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:6a432f04-834c-4e86-9583-e3e6a754a75cEnglishSymplectic Elements at Oxford2011Davies, SIchihara, ORoberts, PThomson, JThe chemo- and enantioselective reduction of ethyl 4-chloroacetoacetate and the diastereoselective conjugate addition of enantiopure lithium N-benzyl-N-(α-methylbenzyl)amide to an α,β-unsaturated ester have been used as the key steps in the total asymmetric syntheses of (+)-negamycin (in 13 steps and 24% overall yield), (+)-3-epi-negamycin (in 13 steps and 10% overall yield) and sperabillin C (in 17 steps and 13% overall yield) from commercially available starting materials. © 2010 Elsevier Ltd. All rights reserved. |
| spellingShingle | Davies, S Ichihara, O Roberts, P Thomson, J Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition |
| title | Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition |
| title_full | Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition |
| title_fullStr | Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition |
| title_full_unstemmed | Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition |
| title_short | Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition |
| title_sort | asymmetric syntheses of negamycin 3 epi negamycin and sperabillin c via lithium amide conjugate addition |
| work_keys_str_mv | AT daviess asymmetricsynthesesofnegamycin3epinegamycinandsperabillincvialithiumamideconjugateaddition AT ichiharao asymmetricsynthesesofnegamycin3epinegamycinandsperabillincvialithiumamideconjugateaddition AT robertsp asymmetricsynthesesofnegamycin3epinegamycinandsperabillincvialithiumamideconjugateaddition AT thomsonj asymmetricsynthesesofnegamycin3epinegamycinandsperabillincvialithiumamideconjugateaddition |