دورية أكاديمية
Total Synthesis of (+)-6-epi-Ophiobolin A.
| العنوان: | Total Synthesis of (+)-6-epi-Ophiobolin A. |
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| المؤلفون: | Thach DQ; Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA., Brill ZG; Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA., Grover HK; Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA., Esguerra KV; Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA., Thompson JK; Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA., Maimone TJ; Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA. |
| المصدر: | Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Jan 20; Vol. 59 (4), pp. 1532-1536. Date of Electronic Publication: 2019 Dec 12. |
| نوع المنشور: | Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
| اللغة: | English |
| بيانات الدورية: | Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: <2004-> : Weinheim : Wiley-VCH Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962- |
| مواضيع طبية MeSH: | Biological Products/*chemical synthesis , Sesterterpenes/*chemical synthesis, Biological Products/chemistry ; Sesterterpenes/chemistry |
| مستخلص: | The ophiobolin sesterterpenes are notable plant pathogens which have recently elicited significant chemical and biological attention because of their intriguing carbogenic frameworks, reactive functionalities, and emerging anticancer profiles. Reported herein is a total synthesis of (+)-6-epi-ophiobolin A in 14 steps, a task which addresses construction of the synthetically challenging spirocyclic tetrahydrofuran motif as well as several other key stereochemical problems. This work demonstrates a streamlined synthetic platform to complex ophiobolins leveraging disparate termination modes of a radical polycyclization cascade for divergent elaboration and functionalization. (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.) |
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| معلومات مُعتمدة: | R01 GM116952 United States GM NIGMS NIH HHS; S10 RR027172 United States RR NCRR NIH HHS; S10 OD024998 United States OD NIH HHS; DGE-1106400 International Directorate for Education and Human Resources |
| فهرسة مساهمة: | Keywords: natural products; radical reactions; spirocycles; terpenes; total synthesis |
| المشرفين على المادة: | 0 (Biological Products) 0 (Sesterterpenes) 4611-05-6 (ophiobolin A) |
| تواريخ الأحداث: | Date Created: 20191107 Date Completed: 20210113 Latest Revision: 20240328 |
| رمز التحديث: | 20240329 |
| مُعرف محوري في PubMed: | PMC6980906 |
| DOI: | 10.1002/anie.201913150 |
| PMID: | 31693792 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1521-3773 |
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| DOI: | 10.1002/anie.201913150 |