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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2014
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th-cmuir.6653943832-44852014-08-30T02:42:28Z Synthesis of castanospermine Machan T. Davis A.S. Liawruangrath B. Pyne S.G. 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. 2014-08-30T02:42:28Z 2014-08-30T02:42:28Z 2008 Article 00404020 10.1016/j.tet.2008.01.073 TETRA http://www.scopus.com/inward/record.url?eid=2-s2.0-39149142197&partnerID=40&md5=fc8cbeb31182e4e76906adca244818ad http://cmuir.cmu.ac.th/handle/6653943832/4485 English |
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English |
| 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 |
Article |
| author |
Machan T. Davis A.S. Liawruangrath B. Pyne S.G. |
| spellingShingle |
Machan T. Davis A.S. Liawruangrath B. Pyne S.G. Synthesis of castanospermine |
| author_facet |
Machan T. Davis A.S. Liawruangrath B. Pyne S.G. |
| author_sort |
Machan T. |
| 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 |
2014 |
| url |
http://www.scopus.com/inward/record.url?eid=2-s2.0-39149142197&partnerID=40&md5=fc8cbeb31182e4e76906adca244818ad http://cmuir.cmu.ac.th/handle/6653943832/4485 |
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1681420246111485952 |