Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange
Abstract The total synthesis of isotopically labelled (9R,10S)-dihydrosterculic acid, a usual cyclopropane fatty acid with biologically relevant toxicity upon desaturation in vivo, is reported. A diastereoselective Corey–Chaykovsky reaction was employed to form the cyclopropane ring. Rapid quenchi...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Georg Thieme Verlag KG
2018-04-01
|
| Series: | SynOpen |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591976 |
| _version_ | 1818289568478134272 |
|---|---|
| author | Samuel W. J. Shields Peter H. Buist Jeffrey M. Manthorpe |
| author_facet | Samuel W. J. Shields Peter H. Buist Jeffrey M. Manthorpe |
| author_sort | Samuel W. J. Shields |
| collection | DOAJ |
| description | Abstract
The total synthesis of isotopically labelled (9R,10S)-dihydrosterculic acid, a usual cyclopropane fatty acid with biologically relevant toxicity upon desaturation in vivo, is reported. A diastereoselective Corey–Chaykovsky reaction was employed to form the cyclopropane ring. Rapid quenching of a lithium-sulfoxide exchange was required to achieve the requisite high levels of deuterium incorporation. |
| first_indexed | 2024-12-13T02:14:21Z |
| format | Article |
| id | doaj.art-2d3c7bfe259b46c889a94febc691f7ac |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-12-13T02:14:21Z |
| publishDate | 2018-04-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-2d3c7bfe259b46c889a94febc691f7ac2022-12-22T00:02:56ZengGeorg Thieme Verlag KGSynOpen2509-93962018-04-0102020168017510.1055/s-0036-1591976Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide ExchangeSamuel W. J. Shields0Peter H. Buist1Jeffrey M. Manthorpe2Carleton University, Department of Chemistry, 203 Steacie Building,Carleton University, Department of Chemistry, 203 Steacie Building,Carleton University, Department of Chemistry, 203 Steacie Building,Abstract The total synthesis of isotopically labelled (9R,10S)-dihydrosterculic acid, a usual cyclopropane fatty acid with biologically relevant toxicity upon desaturation in vivo, is reported. A diastereoselective Corey–Chaykovsky reaction was employed to form the cyclopropane ring. Rapid quenching of a lithium-sulfoxide exchange was required to achieve the requisite high levels of deuterium incorporation.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591976lithium-sulfoxide exchangedeuterium labellingasymmetric corey–chaykovsky cyclopropanationcyclopropane fatty acidsmechanistic probesfatty acid desaturation |
| spellingShingle | Samuel W. J. Shields Peter H. Buist Jeffrey M. Manthorpe Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange SynOpen lithium-sulfoxide exchange deuterium labelling asymmetric corey–chaykovsky cyclopropanation cyclopropane fatty acids mechanistic probes fatty acid desaturation |
| title | Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange |
| title_full | Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange |
| title_fullStr | Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange |
| title_full_unstemmed | Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange |
| title_short | Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange |
| title_sort | asymmetric and regiospecific synthesis of isotopically labelled cyclopropane fatty acid 9r 10s dihydrosterculic acid overcoming spontaneous protonation during lithium sulfoxide exchange |
| topic | lithium-sulfoxide exchange deuterium labelling asymmetric corey–chaykovsky cyclopropanation cyclopropane fatty acids mechanistic probes fatty acid desaturation |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591976 |
| work_keys_str_mv | AT samuelwjshields asymmetricandregiospecificsynthesisofisotopicallylabelledcyclopropanefattyacid9r10sdihydrosterculicacidovercomingspontaneousprotonationduringlithiumsulfoxideexchange AT peterhbuist asymmetricandregiospecificsynthesisofisotopicallylabelledcyclopropanefattyacid9r10sdihydrosterculicacidovercomingspontaneousprotonationduringlithiumsulfoxideexchange AT jeffreymmanthorpe asymmetricandregiospecificsynthesisofisotopicallylabelledcyclopropanefattyacid9r10sdihydrosterculicacidovercomingspontaneousprotonationduringlithiumsulfoxideexchange |