Asymmetric synthesis of (-)-martinellic acid.
A high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3-[2'-(N,N-diallylamino)-5'-bromophenyl]propenoate and alkylation of the resultant β-amino ester have been used...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2013
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| _version_ | 1797051402448535552 |
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| author | Davies, S Fletcher, A Lee, J Lorkin, T Roberts, P Thomson, J |
| author_facet | Davies, S Fletcher, A Lee, J Lorkin, T Roberts, P Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | A high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3-[2'-(N,N-diallylamino)-5'-bromophenyl]propenoate and alkylation of the resultant β-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture. |
| first_indexed | 2024-03-06T18:19:03Z |
| format | Journal article |
| id | oxford-uuid:05a2fb1d-aa19-47dd-b450-5373080e77cd |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:19:03Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | oxford-uuid:05a2fb1d-aa19-47dd-b450-5373080e77cd2022-03-26T08:58:22ZAsymmetric synthesis of (-)-martinellic acid.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:05a2fb1d-aa19-47dd-b450-5373080e77cdEnglishSymplectic Elements at Oxford2013Davies, SFletcher, ALee, JLorkin, TRoberts, PThomson, JA high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3-[2'-(N,N-diallylamino)-5'-bromophenyl]propenoate and alkylation of the resultant β-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture. |
| spellingShingle | Davies, S Fletcher, A Lee, J Lorkin, T Roberts, P Thomson, J Asymmetric synthesis of (-)-martinellic acid. |
| title | Asymmetric synthesis of (-)-martinellic acid. |
| title_full | Asymmetric synthesis of (-)-martinellic acid. |
| title_fullStr | Asymmetric synthesis of (-)-martinellic acid. |
| title_full_unstemmed | Asymmetric synthesis of (-)-martinellic acid. |
| title_short | Asymmetric synthesis of (-)-martinellic acid. |
| title_sort | asymmetric synthesis of martinellic acid |
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