دورية أكاديمية
Total Synthesis of (±)-Aspidospermidine, (±)-Aspidofractinine, (±)-Limaspermidine, and (±)-Vincadifformine via a Cascade and Common Intermediate Strategy.
| العنوان: | Total Synthesis of (±)-Aspidospermidine, (±)-Aspidofractinine, (±)-Limaspermidine, and (±)-Vincadifformine via a Cascade and Common Intermediate Strategy. |
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| المؤلفون: | Cain DL; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, Fife, St AndrewsKY16 9ST, U.K., Anderson NA; GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, StevenageSG1 2NY, U.K., Cordes DB; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, Fife, St AndrewsKY16 9ST, U.K., Slawin AMZ; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, Fife, St AndrewsKY16 9ST, U.K., Watson AJB; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, Fife, St AndrewsKY16 9ST, U.K. |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2022 Nov 18; Vol. 87 (22), pp. 15559-15563. Date of Electronic Publication: 2022 Oct 19. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مواضيع طبية MeSH: | Aspidosperma* , Alkaloids*, Indole Alkaloids ; Stereoisomerism |
| مستخلص: | A concise strategy for the total synthesis of several Aspidosperma alkaloids is reported. A Suzuki-Miyaura cross-coupling provides access to a 2-vinyl indole that undergoes a Diels-Alder cascade reaction with butyn-2-one to deliver a pyrroloindoline intermediate. This undergoes cascade amidation, reduction, skeletal rearrangement, and intramolecular Michael addition to provide a common intermediate containing the full framework of the Aspidosperma alkaloids. The utility of this intermediate is shown in the synthesis of four different natural products. |
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| المشرفين على المادة: | 0 (limaspermidine) 0 (aspidospermidine) 0 (aspidofractinine) 3247-10-7 (vincadifformine) 0 (Indole Alkaloids) 0 (Alkaloids) |
| تواريخ الأحداث: | Date Created: 20221019 Date Completed: 20221121 Latest Revision: 20230106 |
| رمز التحديث: | 20230106 |
| مُعرف محوري في PubMed: | PMC9680024 |
| DOI: | 10.1021/acs.joc.2c02099 |
| PMID: | 36259765 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6904 |
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| DOI: | 10.1021/acs.joc.2c02099 |