General Access to Concave-Substituted cis-Dioxabicyclo[3.3.0]octanones: Enantioselective Total Syntheses of Macfarlandin C and Dendrillolide A
| العنوان: | General Access to Concave-Substituted cis-Dioxabicyclo[3.3.0]octanones: Enantioselective Total Syntheses of Macfarlandin C and Dendrillolide A |
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| المؤلفون: | André P. Dieskau, Peng Zhao, Larry E. Overman, Gregory L. Lackner, Tyler K. Allred |
| المصدر: | The Journal of Organic Chemistry. 85:15532-15551 |
| بيانات النشر: | American Chemical Society (ACS), 2020. |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Enantiopure drug, Double bond, chemistry, Extramural, Stereochemistry, Organic Chemistry, Enantioselective synthesis, Moiety, Stereoselectivity, Stereoisomerism, Stereocenter |
| الوصف: | The evolution of a strategy to access the family of rearranged spongian diterpenoids harboring a concave-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-one fragment is described. The approach involves late-stage fragment coupling of a tertiary-carbon radical and an electron-deficient double bond to form vicinal quaternary and tertiary stereocenters with high fidelity. A stereoselective Mukaiyama hydration is the key step in the subsequent elaboration of the cis-2,8-dioxabicyclo[3.3.0]octan-3-one moiety. This strategy was utilized in enantioselective total syntheses of (-)-macfarlandin C and (+)-dendrillolide A. An efficient construction of enantiopure tetramethyloctahydronaphthalenes was developed during the construction of (-)-macfarlandin C. |
| تدمد: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.0c02273 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::6a727c081d23a284fd8264d924dfd115 https://doi.org/10.1021/acs.joc.0c02273 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi...........6a727c081d23a284fd8264d924dfd115 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15206904 00223263 |
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| DOI: | 10.1021/acs.joc.0c02273 |