Chemie und Biologie von Taxol

Nicolaou, K. C.; Dai, Wei‐Min; Guy, R. Kiplin

doi:10.1002/ange.19941060105

Cited by 142 publications

(35 citation statements)

References 268 publications

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“…With the Vinca alkaloids, paclitaxel (Taxol) and docetaxel (Taxotre), drugs binding to tubulin have already entered clinical use. [43] Another very promising class of antineoplastic agents affecting this subcellular target are the so-called combretastatins, a family of natural products isolated from the South African willow tree Combretum caffrum and closely related species such as C. apiculatum, C. molle, and C. psidioides. [44] Most active among them is the stilbene derivative combretastatin A-4 (40) which is an exceptionally strong inhibitor of tubulin polymerization (IC 50~2 -3 mm) ligating the colchicine binding site of the protein.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition‐Metal Catalyzed Cycloisomerization Reactions

Mamane¹,

Hannen²,

Fürstner³

2004

Chemistry A European J

618

254

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Readily available biphenyl derivatives containing an alkyne unit at one of their ortho-positions are converted into substituted phenanthrenes on exposure to catalytic amounts of either PtCl2, AuCl, AuCl3, GaCl3 or InCl3 in toluene. This 6-endo-dig cyclization likely proceeds through initial pi-complexation of the alkyne unit followed by interception of the resulting eta2-metal species by the adjacent arene ring. The reaction is inherently modular, allowing for substantial structural variations and for the incorporation of substituents at any site of the phenanthrene product. Moreover, it is readily extended to the heterocyclic series as exemplified by the preparation of benzoindoles, benzocarbazoles, naphthothiophenes, as well as bridgehead nitrogen heterocycles such as pyrrolo[1,2-a]quinolines. Depending on the chosen catalyst, biaryls bearing halo-alkyne units can either be converted into the corresponding 10-halo-phenanthrenes or into the isomeric 9-halo-phenanthrenes; in the latter case, the concomitant 1,2-halide shift is best explained by assuming a metal vinylidene species as the reactive intermediate. The scope of this novel method for the preparation of polycyclic arenes is illustrated by the total synthesis of a series of polyoxygenated phenanthrenes that are close relatives of the anticancer agent combretastatin A-4, as well as by the total synthesis of the aporphine alkaloid O-methyl-dehydroisopiline and its naturally occurring symmetrical dimer.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition‐Metal Catalyzed Cycloisomerization Reactions

Mamane¹,

Hannen²,

Fürstner³

2004

Chemistry A European J

618

254

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“…A comparison of the altohyrtins and spongistatins with other natural antineoplastics indicates that there is strong competition. Commercially available drugs such as taxol or taxotere are established; [13] other compounds, for example, the epothilones, are impressive not only because of their excellent cytotoxicity test results, but especially because of their very economic accessability through the cultivation of myxobacteria. [14] The bryostatins, a relatively new class of marine macrolides, are in a way the competition in the own backyard, since the first clinical tests are already underway.…”

Section: Compoundmentioning

confidence: 99%

Spongistatins, Cynachyrolides, or Altohyrtins? Marine Macrolides in Cancer Therapy

Pietruszka

1998

Angewandte Chemie International Edition

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“…Naturstoffen mit antineoplastischen Eigenschaften [16,17] Es ist höchst erstaunlich, dass so weit entfernte Taxa, wie Pilze und höhere Pflanzen, auf dem gleichen Biosyntheseweg Sekundärmetabolite herstellen. Eine plausible Erklärung hierfür ist der horizontale Gentransfer, bei der der Mikroorganismus den Biosyntheseweg entwickelt und die entsprechenden Gene, die in diesem, im Unterschied zu höheren Pflanzen, in der Regel in einem einzigen Gencluster abgelegt sind, in einem Übergang auf die Pflanze über-trägt.…”

Section: Abb 14 Europäische Eibe (Taxus Baccata) (Links) Und Pazifisunclassified

“…Zur Synthese des (2R,3S)-3-Phenylisoserins wurde eine ganze Reihe von effizienten Synthesen entwickelt, von denen nur ausgewählte Beispiele vorgestellt werden sollen [16].…”

Section: Seitenketten-synthesenunclassified

Taxol®. Hoffnung gegen Krebs

Schäfer¹

2011

Chemie in nserer Zeit

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Krebserkrankungen kennt man seit der Antike. Die Entdeckung von Paclitaxel und die Entwicklung von Taxol(r) ist sowohl für die Naturstoffsynthese als auch für die Krebsforschung ein bedeutender Meilenstein. Unmittelbar nach der Entdeckung seiner einzigartigen pharmakologischen Eigenschaften wurde die klinische Versorgung mit Material einer Verbindung mit solch anspruchsvoller Struktur ein ernsthaftes Problem. Namhafte Arbeitskreise lieferten eine Reihe von Totalsynthesen, aber der klinische Bedarf wurde von Anfang an zunächst durch Extraktion der Eibenrinde und später durch Partialsynthese gedeckt. Seit den 1990er Jahren stellt man Paclitaxel zusätzlich durch Pflanzenzellfermentation her.

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Chemie und Biologie von Taxol

Cited by 142 publications

References 268 publications

Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition‐Metal Catalyzed Cycloisomerization Reactions

Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition‐Metal Catalyzed Cycloisomerization Reactions

Spongistatins, Cynachyrolides, or Altohyrtins? Marine Macrolides in Cancer Therapy

Taxol®. Hoffnung gegen Krebs

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