Total Synthesis of Baccatin III and Taxol

Danishefsky, Samuel J.; Masters, b John J.; Young, Charles W.; Snyder, e Lawrence B.; Magee, f Thomas V.; Jung, Guenther; Isaacs, h Richard C. A.; Bornmann, William G.; Alaimo, i Cheryl A.; Coburn, h and Craig A.; Grandi, Martin J. Di

doi:10.1021/ja952692a

Cited by 417 publications

(195 citation statements)

References 47 publications

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“…Besides our total synthesis, a number of other elegant total syntheses of Taxol have been reported by Holton et al [27], Danishefsky et al [28], Wender et al [29], Mukaiyama et al [30] and Kuwajima and co-workers [31]. Collectively, these accomplishments advanced the art and science of organic synthesis, enabled the design and synthesis of numerous analogues of Taxol, and facilitated biological investigations and drug discovery efforts in the area, including identification of biological tools and drug candidates.…”

Section: The Total Synthesis Of Taxolmentioning

confidence: 75%

Organic synthesis: the art and science of replicating the molecules of living nature and creating others like them in the laboratory

Nicolaou

2014

Proc. R. Soc. A.

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Section: The Total Synthesis Of Taxolmentioning

confidence: 75%

Organic synthesis: the art and science of replicating the molecules of living nature and creating others like them in the laboratory

Nicolaou

2014

Proc. R. Soc. A.

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“…One of the interesting reactions to synthesize substituted biphenyls 1 involves the Suzuki cross-coupling reaction, a protocol of which has been disclosed elsewhere. 2 The carbon-carbon bond construction method 3,4,5,6 in organic synthesis has allowed chemists to assemble complex molecular frameworks to prepare numerous natural products, 7 drug precursors, 8 biological compounds, 9 organic products 10 and herbicides. 11 Lately, the conditions developed for the cross-coupling reaction have many desirable features for large scale syntheses and are persuasively used in the industrial synthesis of pharmaceutical and chemical products.…”

Section: Introductionmentioning

confidence: 99%

Reaction Monitoring by Means of Multivariate Data Analysis of Near-Infrared and Raman Spectra

Hetemi

Janagap²

2017

ACSi

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An efficient, versatile and non-destructive in situ method in reaction monitoring using vibrational spectroscopy is described. A Suzuki cross-coupling reaction was monitored in which the substrate 1-iodo-2-nitrobenzene reacted with the electrophile phenylboronic acid to form the product 2-nitrobiphenyl. To hasten the reaction, palladium(II) acetate and potassium carbonate were added to serve as catalyst and to promote transmetalation, respectively. This reaction was monitored using near-infrared and Raman spectroscopy. The recorded data was subjected to multivariate analysis such as principal component analysis in order to detect spectral changes due to the formation of the product. To confirm the presence of the desired product, offline analyses were performed using gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy. The results demonstrate how Raman spectroscopy is able to detect the formation of the product in real time, whereas near-infrared spectroscopy fails to do so.

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“…The palladium-catalyzed cross-coupling of olefins with aryl or vinyl halides, known as the Heck reaction, is a well-known example for forming carbon-carbon bonds or introducing functional groups into substrate molecules. The Heck reaction has found applications in the preparation of a wide spectrum of organic chemicals, materials, and natural products [1][2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Carbon-Carbon Cross-Coupling Reactions in Thermomorphous Double Emulsions

Misuk¹,

Mai²,

Γιαννόπουλος³

et al. 2015

J Flow Chem

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The method of combining the concept of fluorous biphasic catalysis (FCB) with micro multiple emulsions benefits from the advantages of homogeneous as well as from heterogeneous catalysis in continuous micro flow. In this particular case, three immiscible fluid phases in continuous micro segmented flow were used to perform palladium-catalyzed Heck crosscoupling reactions of styrene with aryl halides. A capillary tube-in-tube coaxial flow setup in combination with a glass micro reactor was used to produce monodisperse aqueous phase/organic phase/perfluorinated phase double emulsions. The resulting emulsions had a core-shell droplet structure composed of a perfluorcarbon fluid in which a palladium catalyst with fluorinated phosphine ligands was dissolved, an organic phase consisting of a solvent and two reagents, and an alkaline aqueous solution. The fluorous and organic phases of the double emulsion form a thermomorphous system which can be converted into one phase by an increase of temperature above 150°C, and the catalytic reaction is performed temporarily. By decreasing the temperature, a phase separation takes place; after that, the organic phase contains the product and the catalyst is located in the fluorous phase. The separated catalyst solution was reused several times without a noticeable loss of activity. The main advantage of this method is to use temporarily very high catalyst concentrations in each droplet, while employing only small amounts of the catalyst for the overall reaction volume.

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Total Synthesis of Baccatin III and Taxol

Cited by 417 publications

References 47 publications

Organic synthesis: the art and science of replicating the molecules of living nature and creating others like them in the laboratory

Organic synthesis: the art and science of replicating the molecules of living nature and creating others like them in the laboratory

Reaction Monitoring by Means of Multivariate Data Analysis of Near-Infrared and Raman Spectra

Palladium-Catalyzed Carbon-Carbon Cross-Coupling Reactions in Thermomorphous Double Emulsions

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