دورية أكاديمية
Synthesis of Breitfussin B by Late-Stage Bromination
| العنوان: | Synthesis of Breitfussin B by Late-Stage Bromination |
|---|---|
| المؤلفون: | Khan, Akbar H., Chen, Jason |
| المصدر: | Chemistry Publications |
| بيانات النشر: | Iowa State University Digital Repository |
| سنة النشر: | 2015 |
| المجموعة: | Digital Repository @ Iowa State University |
| مصطلحات موضوعية: | Materials Chemistry, Other Chemistry, Physical Chemistry |
| الوصف: | The breitfussins are halogenated natural products whose structures were determined with the assistance of atomic-force microscopy. The site selectivity of N-bromosuccinimide-mediated bromination of a model breitfussin core was found to be strongly dependent on solvent selection; use of acetone led to oxazole bromination, and use of a pyridine-containing mixture led to pyrrole bromination. This tunable site-selective bromination was used in a protecting-group-free synthesis of breitfussin B that proceeded in 9.2% yield over 12 reactions and five chromatographic separations. A bromooxazole analogue of breitfussin A was also prepared by late-stage bromination but isomerized on silica gel to form breitfussin B. This isomerization appeared to proceed through a unimolecular pathway. |
| نوع الوثيقة: | text |
| وصف الملف: | application/pdf |
| اللغة: | English |
| العلاقة: | https://lib.dr.iastate.edu/chem_pubs/891Test; https://lib.dr.iastate.edu/cgi/viewcontent.cgi?article=1900&context=chem_pubsTest |
| الإتاحة: | https://lib.dr.iastate.edu/chem_pubs/891Test https://lib.dr.iastate.edu/cgi/viewcontent.cgi?article=1900&context=chem_pubsTest |
| رقم الانضمام: | edsbas.B22675E1 |
| قاعدة البيانات: | BASE |
| الوصف غير متاح. |