Chemoenzymatic synthesis of the enantiomers of desoxymuscarine
Two different chemoenzymatic approaches allowed the preparation of the enantiomers of desoxymuscarine 5, a muscarinic receptor agonist. Transesterification of racemic 5-hexen-2-ol 7 with vinyl butyrate under the catalysis of Candida antarctica B lipase was the key step for the preparation of (-)-5 (...
| Published in: | Tetrahedron: Asymmetry |
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| Main Authors: | , , , , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
PERGAMON-ELSEVIER SCIENCE LTD
1998
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| Subjects: | |
| Online Access: | http://hdl.handle.net/2434/183323 https://doi.org/10.1016/S0957-4166(98)00010-X |
| _version_ | 1821769351720599552 |
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| author | P. Conti C. Dallanoce M. De Amici C. De Micheli G. Carrea F. Zambianchi |
| author2 | P. Conti C. Dallanoce M. De Amici C. De Micheli G. Carrea F. Zambianchi |
| author_facet | P. Conti C. Dallanoce M. De Amici C. De Micheli G. Carrea F. Zambianchi |
| author_sort | P. Conti |
| collection | The University of Milan: Archivio Istituzionale della Ricerca (AIR) |
| container_issue | 4 |
| container_start_page | 657 |
| container_title | Tetrahedron: Asymmetry |
| container_volume | 9 |
| description | Two different chemoenzymatic approaches allowed the preparation of the enantiomers of desoxymuscarine 5, a muscarinic receptor agonist. Transesterification of racemic 5-hexen-2-ol 7 with vinyl butyrate under the catalysis of Candida antarctica B lipase was the key step for the preparation of (-)-5 (2R,5R). On the other hand, lipase PS-catalyzed hydrolysis of iodo butyrate (+/-)-14 was utilized to obtain (+)-5 (2S,5S). Both enantiomers were prepared with enantiomeric excesses higher than 98\%. (C) 1998 Elsevier Science Ltd. All rights reserved. |
| format | Article in Journal/Newspaper |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| id | ftunivmilanoair:oai:air.unimi.it:2434/183323 |
| institution | Open Polar |
| language | English |
| op_collection_id | ftunivmilanoair |
| op_container_end_page | 665 |
| op_doi | https://doi.org/10.1016/S0957-4166(98)00010-X |
| op_relation | info:eu-repo/semantics/altIdentifier/wos/WOS:000072692400017 volume:9 issue:4 firstpage:657 lastpage:665 journal:TETRAHEDRON-ASYMMETRY http://hdl.handle.net/2434/183323 doi:10.1016/S0957-4166(98)00010-X info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-0032570512 |
| publishDate | 1998 |
| publisher | PERGAMON-ELSEVIER SCIENCE LTD |
| record_format | openpolar |
| spelling | ftunivmilanoair:oai:air.unimi.it:2434/183323 2025-01-16T19:36:21+00:00 Chemoenzymatic synthesis of the enantiomers of desoxymuscarine P. Conti C. Dallanoce M. De Amici C. De Micheli G. Carrea F. Zambianchi P. Conti C. Dallanoce M. De Amici C. De Micheli G. Carrea F. Zambianchi 1998 http://hdl.handle.net/2434/183323 https://doi.org/10.1016/S0957-4166(98)00010-X eng eng PERGAMON-ELSEVIER SCIENCE LTD place:THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND info:eu-repo/semantics/altIdentifier/wos/WOS:000072692400017 volume:9 issue:4 firstpage:657 lastpage:665 journal:TETRAHEDRON-ASYMMETRY http://hdl.handle.net/2434/183323 doi:10.1016/S0957-4166(98)00010-X info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-0032570512 Settore CHIM/08 - Chimica Farmaceutica info:eu-repo/semantics/article 1998 ftunivmilanoair https://doi.org/10.1016/S0957-4166(98)00010-X 2024-03-27T16:31:57Z Two different chemoenzymatic approaches allowed the preparation of the enantiomers of desoxymuscarine 5, a muscarinic receptor agonist. Transesterification of racemic 5-hexen-2-ol 7 with vinyl butyrate under the catalysis of Candida antarctica B lipase was the key step for the preparation of (-)-5 (2R,5R). On the other hand, lipase PS-catalyzed hydrolysis of iodo butyrate (+/-)-14 was utilized to obtain (+)-5 (2S,5S). Both enantiomers were prepared with enantiomeric excesses higher than 98\%. (C) 1998 Elsevier Science Ltd. All rights reserved. Article in Journal/Newspaper Antarc* Antarctica The University of Milan: Archivio Istituzionale della Ricerca (AIR) Tetrahedron: Asymmetry 9 4 657 665 |
| spellingShingle | Settore CHIM/08 - Chimica Farmaceutica P. Conti C. Dallanoce M. De Amici C. De Micheli G. Carrea F. Zambianchi Chemoenzymatic synthesis of the enantiomers of desoxymuscarine |
| title | Chemoenzymatic synthesis of the enantiomers of desoxymuscarine |
| title_full | Chemoenzymatic synthesis of the enantiomers of desoxymuscarine |
| title_fullStr | Chemoenzymatic synthesis of the enantiomers of desoxymuscarine |
| title_full_unstemmed | Chemoenzymatic synthesis of the enantiomers of desoxymuscarine |
| title_short | Chemoenzymatic synthesis of the enantiomers of desoxymuscarine |
| title_sort | chemoenzymatic synthesis of the enantiomers of desoxymuscarine |
| topic | Settore CHIM/08 - Chimica Farmaceutica |
| topic_facet | Settore CHIM/08 - Chimica Farmaceutica |
| url | http://hdl.handle.net/2434/183323 https://doi.org/10.1016/S0957-4166(98)00010-X |