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....
محفوظ في:
| المؤلفون الرئيسيون: | , , , |
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| التنسيق: | مقال |
| اللغة: | English |
| منشور في: |
2014
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| الوصول للمادة أونلاين: | http://www.scopus.com/inward/record.url?eid=2-s2.0-39149142197&partnerID=40&md5=fc8cbeb31182e4e76906adca244818ad http://cmuir.cmu.ac.th/handle/6653943832/4485 |
| الوسوم: |
إضافة وسم
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| المؤسسة: | Chiang Mai University |
| اللغة: | English |
| الملخص: | 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. |
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