Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis
A concise and diastereoselective total synthesis of tetraketide and euscapholide is described in ten steps in 10.6% overall yield from acetaldehyde and (S)-pent-4-ene-1,2-diol. Jacobsen hydrolytic kinetic resolution, Prins cyclization, ring-closing metathesis and oxa-Michael addition reactions are...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Georg Thieme Verlag KG
2022-11-01
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| Series: | SynOpen |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0042-1751381 |
| _version_ | 1811305120327008256 |
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| author | Dhanraj O. Biradar Yogesh D. Mane Basi V. Subba Reddy |
| author_facet | Dhanraj O. Biradar Yogesh D. Mane Basi V. Subba Reddy |
| author_sort | Dhanraj O. Biradar |
| collection | DOAJ |
| description | A concise and diastereoselective total synthesis of tetraketide and euscapholide is described in ten steps in 10.6% overall yield from acetaldehyde and (S)-pent-4-ene-1,2-diol. Jacobsen hydrolytic kinetic resolution, Prins cyclization, ring-closing metathesis and oxa-Michael addition reactions are the key steps involved in the synthesis. |
| first_indexed | 2024-04-13T08:19:43Z |
| format | Article |
| id | doaj.art-fb2fdddb24a74b2c86a21c3f28aacdba |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-04-13T08:19:43Z |
| publishDate | 2022-11-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-fb2fdddb24a74b2c86a21c3f28aacdba2022-12-22T02:54:41ZengGeorg Thieme Verlag KGSynOpen2509-93962022-11-01060431231810.1055/s-0042-1751381Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing MetathesisDhanraj O. Biradar0Yogesh D. Mane1Basi V. Subba Reddy2Indian Institute of Chemical TechnologyBSS Arts, Science & Commerce CollegeIndian Institute of Chemical TechnologyA concise and diastereoselective total synthesis of tetraketide and euscapholide is described in ten steps in 10.6% overall yield from acetaldehyde and (S)-pent-4-ene-1,2-diol. Jacobsen hydrolytic kinetic resolution, Prins cyclization, ring-closing metathesis and oxa-Michael addition reactions are the key steps involved in the synthesis.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0042-1751381prins cyclizationeuscapholidetetraketidering-closing metathesis |
| spellingShingle | Dhanraj O. Biradar Yogesh D. Mane Basi V. Subba Reddy Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis SynOpen prins cyclization euscapholide tetraketide ring-closing metathesis |
| title | Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis |
| title_full | Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis |
| title_fullStr | Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis |
| title_full_unstemmed | Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis |
| title_short | Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis |
| title_sort | stereoselective synthesis of euscapholide and tetraketide via prins cyclisation and ring closing metathesis |
| topic | prins cyclization euscapholide tetraketide ring-closing metathesis |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0042-1751381 |
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