Synthesis of castanospermine
The diastereoselective synthesis of castanospermine is described in 11 synthetic steps from l-xylose. The borono-Mannich reaction between l-xylose, allylamine, and (E)-styrene boronic acid gives a tetrahydroxy amine with the desired configurations for C-6, C-7, C-8, and C-8a in the target molecule....
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2018
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th-cmuir.6653943832-601782018-09-10T03:47:55Z Synthesis of castanospermine Theeraphan Machan Andrew S. Davis Boonsom Liawruangrath Stephen G. Pyne Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics The diastereoselective synthesis of castanospermine is described in 11 synthetic steps from l-xylose. The borono-Mannich reaction between l-xylose, allylamine, and (E)-styrene boronic acid gives a tetrahydroxy amine with the desired configurations for C-6, C-7, C-8, and C-8a in the target molecule. A novel pyrrolo[1,2-c]oxazol-3-one precursor was employed to allow for the control of π-facial diastereoselectivity in an osmium(VIII)-catalyzed syn-dihydroxylation (DH) reaction. A regioselective ring-opening of the cyclic sulfate derivative of the resulting diol then secured the C-1 hydroxyl group of castanospermine with the correct configuration. A Mitsunobu cyclization then provided di-O-benzyl castanospermine and ultimately the final target alkaloid. Crown Copyright © 2008. 2018-09-10T03:39:01Z 2018-09-10T03:39:01Z 2008-03-17 Journal 00404020 2-s2.0-39149142197 10.1016/j.tet.2008.01.073 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=39149142197&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/60178 |
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Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics |
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Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics Theeraphan Machan Andrew S. Davis Boonsom Liawruangrath Stephen G. Pyne Synthesis of castanospermine |
| description |
The diastereoselective synthesis of castanospermine is described in 11 synthetic steps from l-xylose. The borono-Mannich reaction between l-xylose, allylamine, and (E)-styrene boronic acid gives a tetrahydroxy amine with the desired configurations for C-6, C-7, C-8, and C-8a in the target molecule. A novel pyrrolo[1,2-c]oxazol-3-one precursor was employed to allow for the control of π-facial diastereoselectivity in an osmium(VIII)-catalyzed syn-dihydroxylation (DH) reaction. A regioselective ring-opening of the cyclic sulfate derivative of the resulting diol then secured the C-1 hydroxyl group of castanospermine with the correct configuration. A Mitsunobu cyclization then provided di-O-benzyl castanospermine and ultimately the final target alkaloid. Crown Copyright © 2008. |
| format |
Journal |
| author |
Theeraphan Machan Andrew S. Davis Boonsom Liawruangrath Stephen G. Pyne |
| author_facet |
Theeraphan Machan Andrew S. Davis Boonsom Liawruangrath Stephen G. Pyne |
| author_sort |
Theeraphan Machan |
| title |
Synthesis of castanospermine |
| title_short |
Synthesis of castanospermine |
| title_full |
Synthesis of castanospermine |
| title_fullStr |
Synthesis of castanospermine |
| title_full_unstemmed |
Synthesis of castanospermine |
| title_sort |
synthesis of castanospermine |
| publishDate |
2018 |
| url |
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=39149142197&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/60178 |
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1681425387854233600 |