Asymmetric synthesis of (-)-(S,S)-homaline
The asymmetric synthesis of (-)-(S,S)-homaline was achieved in 8 steps from commercially available starting materials using the diastereoselective conjugate addition of the novel lithium amide reagent lithium (R)-N-(3-chloropropyl)-N-(α-methyl-p-methoxybenzyl)amide to methyl cinnamate to install the...
| 主要な著者: | , , , , |
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| フォーマット: | Journal article |
| 言語: | English |
| 出版事項: |
2012
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| _version_ | 1826257745993531392 |
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| author | Davies, S Lee, J Roberts, P Stonehouse, J Thomson, J |
| author_facet | Davies, S Lee, J Roberts, P Stonehouse, J Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The asymmetric synthesis of (-)-(S,S)-homaline was achieved in 8 steps from commercially available starting materials using the diastereoselective conjugate addition of the novel lithium amide reagent lithium (R)-N-(3-chloropropyl)-N-(α-methyl-p-methoxybenzyl)amide to methyl cinnamate to install the correct stereochemistry. Subsequent functional group manipulation of the resultant β-amino ester and Sb(OEt) 3- mediated macrolactamisation was followed by homodimerisation to give (-)-(S,S)-homaline in 18% overall yield, representing the first asymmetric, and by far the most efficient synthesis of this natural product reported to date. © 2011 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-06T18:23:02Z |
| format | Journal article |
| id | oxford-uuid:06f618d1-a1c1-41c8-838d-a8fb2aa703b8 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:23:02Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:06f618d1-a1c1-41c8-838d-a8fb2aa703b82022-03-26T09:05:11ZAsymmetric synthesis of (-)-(S,S)-homalineJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:06f618d1-a1c1-41c8-838d-a8fb2aa703b8EnglishSymplectic Elements at Oxford2012Davies, SLee, JRoberts, PStonehouse, JThomson, JThe asymmetric synthesis of (-)-(S,S)-homaline was achieved in 8 steps from commercially available starting materials using the diastereoselective conjugate addition of the novel lithium amide reagent lithium (R)-N-(3-chloropropyl)-N-(α-methyl-p-methoxybenzyl)amide to methyl cinnamate to install the correct stereochemistry. Subsequent functional group manipulation of the resultant β-amino ester and Sb(OEt) 3- mediated macrolactamisation was followed by homodimerisation to give (-)-(S,S)-homaline in 18% overall yield, representing the first asymmetric, and by far the most efficient synthesis of this natural product reported to date. © 2011 Elsevier Ltd. All rights reserved. |
| spellingShingle | Davies, S Lee, J Roberts, P Stonehouse, J Thomson, J Asymmetric synthesis of (-)-(S,S)-homaline |
| title | Asymmetric synthesis of (-)-(S,S)-homaline |
| title_full | Asymmetric synthesis of (-)-(S,S)-homaline |
| title_fullStr | Asymmetric synthesis of (-)-(S,S)-homaline |
| title_full_unstemmed | Asymmetric synthesis of (-)-(S,S)-homaline |
| title_short | Asymmetric synthesis of (-)-(S,S)-homaline |
| title_sort | asymmetric synthesis of s s homaline |
| work_keys_str_mv | AT daviess asymmetricsynthesisofsshomaline AT leej asymmetricsynthesisofsshomaline AT robertsp asymmetricsynthesisofsshomaline AT stonehousej asymmetricsynthesisofsshomaline AT thomsonj asymmetricsynthesisofsshomaline |