The Catalytic Alkylative Desymmetrization of Anhydrides in a Formal Synthesis of Ionomycin
| العنوان: | The Catalytic Alkylative Desymmetrization of Anhydrides in a Formal Synthesis of Ionomycin |
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| المؤلفون: | Tomislav Rovis, Brian M. Cochran, Matthew J. Cook, Kevin M. Oberg |
| المصدر: | Synthesis. 50:4343-4350 |
| بيانات النشر: | Georg Thieme Verlag KG, 2018. |
| سنة النشر: | 2018 |
| مصطلحات موضوعية: | 010405 organic chemistry, Chemistry, Organic Chemistry, Synthon, Enantioselective synthesis, Oxocarbenium, Diastereomer, Total synthesis, 010402 general chemistry, 01 natural sciences, Enol, Combinatorial chemistry, Desymmetrization, Catalysis, 0104 chemical sciences, Stereocenter, chemistry.chemical_compound |
| الوصف: | The catalytic desymmetrization of anhydrides with zinc reagents provides access to deoxypolypropionate and polypropionate synthons. A synthesis of ionomycin was pursued in which three of the four fragments were assembled using this methodology. Two of the strategies (enol silane/oxocarbenium coupling and reductive cyclization) were not successful at installing the C23 stereocenter, but this stereochemical issue was overcome through a reduction/SN2 approach. In addition to the synthesis of a protected diastereomer of ionomycin, the synthesis of a C17–C32 fragment constitutes a formal total synthesis. |
| تدمد: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0037-1610108 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::1d6cd4a89ff180d70381b9cc679b347c https://doi.org/10.1055/s-0037-1610108 |
| رقم الانضمام: | edsair.doi...........1d6cd4a89ff180d70381b9cc679b347c |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 1437210X 00397881 |
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| DOI: | 10.1055/s-0037-1610108 |