دورية أكاديمية
أعرض في EDS

Total synthesis and isolation of citrinalin and cyclopiamine congeners.

التفاصيل البيبلوغرافية
العنوان: Total synthesis and isolation of citrinalin and cyclopiamine congeners.
المؤلفون: Mercado-Marin EV; Department of Chemistry, University of California, Berkeley, CA 94720, USA., Garcia-Reynaga P; Department of Chemistry, University of California, Berkeley, CA 94720, USA., Romminger S; Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, CP 780, CEP 13560-970, Sao Carlos, SP, Brazil., Pimenta EF; Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, CP 780, CEP 13560-970, Sao Carlos, SP, Brazil., Romney DK; Department of Chemistry, Yale University, P. O. Box 208107, New Haven, Connecticut 06520, USA., Lodewyk MW; Department of Chemistry, University of California, Davis, CA 95616, USA., Williams DE; Department of Chemistry and Earth and Ocean Sciences, University of British Columbia, Vancouver, British Columbia, V6T IZI, Canada., Andersen RJ; Department of Chemistry and Earth and Ocean Sciences, University of British Columbia, Vancouver, British Columbia, V6T IZI, Canada., Miller SJ; Department of Chemistry, Yale University, P. O. Box 208107, New Haven, Connecticut 06520, USA., Tantillo DJ; Department of Chemistry, University of California, Davis, CA 95616, USA., Berlinck RGS; Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, CP 780, CEP 13560-970, Sao Carlos, SP, Brazil., Sarpong R; Department of Chemistry, University of California, Berkeley, CA 94720, USA.
المصدر: Nature [Nature] 2014 May 15; Vol. 509 (7500), pp. 318-324.
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: Nature Publishing Group Country of Publication: England NLM ID: 0410462 Publication Model: Print Cited Medium: Internet ISSN: 1476-4687 (Electronic) Linking ISSN: 00280836 NLM ISO Abbreviation: Nature Subsets: MEDLINE
أسماء مطبوعة: Publication: Basingstoke : Nature Publishing Group
Original Publication: London, Macmillan Journals ltd.
مواضيع طبية MeSH: Alkaloids/*chemical synthesis , Alkaloids/*isolation & purification , Biological Products/*chemical synthesis , Indole Alkaloids/*chemical synthesis , Indole Alkaloids/*isolation & purification , Indolizidines/*chemical synthesis , Indolizidines/*isolation & purification, Alkaloids/biosynthesis ; Alkaloids/chemistry ; Biological Products/chemistry ; Chemistry Techniques, Synthetic ; Indole Alkaloids/chemistry ; Indole Alkaloids/metabolism ; Indolizidines/chemistry ; Indolizidines/metabolism ; Molecular Structure ; Nitrogen/chemistry ; Oxidation-Reduction ; Oxygen/metabolism ; Stereoisomerism
مستخلص: Many natural products that contain basic nitrogen atoms--for example alkaloids like morphine and quinine-have the potential to treat a broad range of human diseases. However, the presence of a nitrogen atom in a target molecule can complicate its chemical synthesis because of the basicity of nitrogen atoms and their susceptibility to oxidation. Obtaining such compounds by chemical synthesis can be further complicated by the presence of multiple nitrogen atoms, but it can be done by the selective introduction and removal of functional groups that mitigate basicity. Here we use such a strategy to complete the chemical syntheses of citrinalin B and cyclopiamine B. The chemical connections that have been realized as a result of these syntheses, in addition to the isolation of both 17-hydroxycitrinalin B and citrinalin C (which contains a bicyclo[2.2.2]diazaoctane structural unit) through carbon-13 feeding studies, support the existence of a common bicyclo[2.2.2]diazaoctane-containing biogenetic precursor to these compounds, as has been proposed previously.
التعليقات: Comment in: Nature. 2014 May 15;509(7500):293-4. (PMID: 24828184)
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معلومات مُعتمدة: R01 GM096403 United States GM NIGMS NIH HHS; S10 RR027172 United States RR NCRR NIH HHS; S10-RR027172 United States RR NCRR NIH HHS; R01 086374 United States PHS HHS; GM096403 United States GM NIGMS NIH HHS
المشرفين على المادة: 0 (Alkaloids)
0 (Biological Products)
0 (Indole Alkaloids)
0 (Indolizidines)
0 (citrinalin B)
N762921K75 (Nitrogen)
S88TT14065 (Oxygen)
تواريخ الأحداث: Date Created: 20140516 Date Completed: 20140731 Latest Revision: 20211021
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC4117207
DOI: 10.1038/nature13273
PMID: 24828190
قاعدة البيانات: MEDLINE
الوصف
تدمد:1476-4687
DOI:10.1038/nature13273