Totalsynthese von Woodrosin I Diese Arbeit wurde von der Deutschen Forschungsgemeinschaft (Leibniz-Programm) und dem Fonds der Chemischen Industrie unterstützt. Wir danken Professor K. Miyahara, Osaka, Japan, für eine Probe des nahe verwandten Naturstoffs Woodrosin II zu Vergleichszwecken sowie Frau K. Radkowski für ihre wertvolle Mitarbeit in verschiedenen Stadien dieses Projekts.

Fürstner, Alois; Jeanjean, Fabien; Razon, Patrick

doi:10.1002/1521-3757(20020617)114:12<2203::aid-ange2203>3.0.co;2-m

Cited by 44 publications

(6 citation statements)

References 10 publications

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“…Outlined below is an unambiguous assignment of the stereostructure of glucolipsin A by comparison of the published data with those of all conceivable C 2 -symmetrical dimers of this type. As part of a long-term project on bioactive glycoconjugates, − we prepared this set of compounds by a highly integrated synthesis route based on a template-directed cyclodimerization reaction as the key step. In contrast to previous assumptions, however, this study revealed that the fatty acid moiety of glucolipsin A comprises a syn -aldol with a (3 S )-configured stereocenter, opposite the (3 R )-configured motif found in cycloviracin 2 .…”

Section: Introductionmentioning

confidence: 99%

Structure Assignment, Total Synthesis, and Evaluation of the Phosphatase Modulating Activity of Glucolipsin A

et al. 2003

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The previously unknown stereostructure of glucolipsin A (1), a complex glycolipid endowed with glucokinase-activating properties, was unambiguously elucidated as (2R,2'R,3S,3'S) by comparison of its spectroscopic and analytical data with those of all conceivable C(2)-symmetric stereoisomers. This set of macrodiolides was prepared by a sequence comprising auxiliary guided aldol reactions, glycosidation of the resulting beta-hydroxy acid derivatives with trichloroacetimidate 7, followed by hydrolytic cleavage of the auxiliaries used. The hydroxy acids thus formed were subjected to a macrodilactonization reaction mediated by 2-chloro-1,3-dimethylimidazolinium chloride (22) as the activating agent; this transformation is highly productive only in the presence of admixed potassium cations which likely serve as templates to preorganize two substrate molecules in a favorable head-to-tail arrangement. Glucolipsin and analogues were subjected to enzymatic assays that revealed that glycoconjugates of this type effectively inhibit the activity of the dual specific phosphatase Cdc25A with IC(50) values in the low micromolar range, while being hardly active against the tyrosine phosphatase PTP1B in vitro. This activity profile was compared to that of other glycolipids previously prepared in this laboratory, including cycloviracin B(1) (2), caloporoside (38), woodrosin I (39), sophorolipid lactone (40), and tricolorin G (41).

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Section: Introductionmentioning

confidence: 99%

Structure Assignment, Total Synthesis, and Evaluation of the Phosphatase Modulating Activity of Glucolipsin A

et al. 2003

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“…Thereafter the Fürstner group expanded rapidly, initial emphasis being on RCM‐based syntheses of complex natural products, woodrosin I (Scheme )45a and iejimalide45b,c being two of many examples. Parallel to these activities, the catalysts themselves were structurally modified (including fine‐tuning of N ‐heterocyclic carbene ligands) and subsequently used by Fürstner’s co‐workers and by many groups worldwide.…”

Section: Alois Fürstner As Director Of the Department Of Organometmentioning

confidence: 99%

“… Top: Structure of woodrosin I with the indicated site of RCM sufficiently removed from possibly interfering functional groups and the novel indenylidene–ruthenium catalyst developed in the Fürstner group 45a. Bottom: Structure of iejimalide featuring the site of RCM and the catalyst used in the ring‐closing process 45b,c.…”

Section: Alois Fürstner As Director Of the Department Of Organometmentioning

confidence: 99%

One Hundred Years of the Max‐Planck‐Institut für Kohlenforschung

Reetz

2014

Angew Chem Int Ed

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This Essay is an account of the institutional and scientific development of the Max‐Planck‐Institut für Kohlenforschung in Mülheim an der Ruhr (Germany), which is the successor to the Kaiser‐Wilhelm‐Institut für Kohlenforschung founded in 1914. The Essay is divided into four main parts, corresponding to the four major periods which are closely associated with the respective Directors of the Institute from 1914 to 2014: 1) Franz Fischer; 2) Karl Ziegler; 3) Günther Wilke; and 4) the period beginning with Manfred T. Reetz, who established a directorate comprising five Directors of equal status, each heading a different research department under the banner of catalysis. Along with key historical events associated with the Institute, research highlights of the four periods are featured.

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“…Hiernach expandierte die Fürstner‐Gruppe rapide, wobei zunächst der Schwerpunkt auf der RCM‐basierten Synthese von Naturstoffen lag. Woodrosin I45a und Iejimalid45b,c seien hier als zwei von vielen Beispielen erwähnt (Schema ). Parallel zu diesen Arbeiten wurden die Katalysatoren selbst strukturell modifiziert (darunter die Feinabstimmung N‐heterocyclischer Carbenliganden) und daraufhin von Fürstners Mitarbeitern und vielen Gruppen weltweit genutzt.…”

Section: Alois Fürstner Als Direktor Der Abteilung Für Metallorganunclassified

“… Oben: Struktur von Woodrosin I mit der angezeigten Stelle für RCM (weit von möglicherweise störenden funktionellen Gruppen) und der neuartige, von der Fürstner‐Gruppe hergestellte Indenyliden‐Ru‐Katalysator 45a. Unten: Struktur von Iejimalid mit der RCM‐Stelle und dem im Ringschlussprozess verwendeten Katalysator 45b,c.…”

Section: Alois Fürstner Als Direktor Der Abteilung Für Metallorganunclassified

100 Jahre Max‐Planck‐Institut für Kohlenforschung

Reetz

2014

Angewandte Chemie

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Dieser Essay beschreibt die institutionelle und wissenschaftliche Entwicklung des Max‐Planck‐Instituts für Kohlenforschung in Mülheim an der Ruhr, des Nachfolge‐Instituts des 1914 gegründeten Kaiser‐Wilhelm‐Instituts für Kohlenforschung. Die vier Hauptteile des Essays entsprechen den vier historischen Perioden, die mit den jeweiligen Direktoren zusammenhängen: 1) Franz Fischer; 2) Karl Ziegler; 3) Günther Wilke; 4) die von Manfred T. Reetz initiierte Umstrukturierung, in deren Folge ein Direktorium bestehend aus fünf gleichberechtigten Direktoren mit jeweils einer Abteilung etabliert wurde. Zusätzlich zu den rein historischen und politischen Entwicklungen werden auch Höhepunkte der Forschung aus den vier Perioden beschrieben.

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Cited by 44 publications

References 10 publications

Structure Assignment, Total Synthesis, and Evaluation of the Phosphatase Modulating Activity of Glucolipsin A

Structure Assignment, Total Synthesis, and Evaluation of the Phosphatase Modulating Activity of Glucolipsin A

One Hundred Years of the Max‐Planck‐Institut für Kohlenforschung

100 Jahre Max‐Planck‐Institut für Kohlenforschung

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