Improved protection and esterification of a precursor of the taxotere® and taxol side chains

Commerçon, Alain; Bézard, D.; Bernard, Faviola; Bourzat, Jean‐Dominique

doi:10.1016/s0040-4039(00)79128-3

Cited by 128 publications

(28 citation statements)

References 12 publications

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“…Reaction of trans-glycidic ester (2a) with 2-nitroaniline(14) The reaction was carried out in silica gel chromatography column. Stirring of the reaction mixture with the slurry of SiO 2 gave similar result.No nitro ester 15-t or 15-e was obtained.…”

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confidence: 99%

Applications of Lewis acids for the efficient syntheses of diltiazem, cephems, and taxoids

Hashiyama

2000

Med. Res. Rev.

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An efficient method is described for preparation of diltiazem hydrochloride (Herbesser®), a marketed calcium antagonist widely used for the treatment of ischemic heart disease. In the reaction of 2‐nitrothiophenol (1) with trans‐3‐phenylglycidic esters (2) carrying various substituents on the benzene ring, both reactivity and stereoselectivity of the oxirane ring‐opening of the glycidates were markedly influenced by the electronic nature of the substituents. As a result of our investigation on the catalytic effect of various Lewis acids in the reaction of 2a with 1, tin compounds were found to be effective catalysts for the cis‐opening and readily produced the threo‐nitro ester (3a‐t), a key intermediate for the synthesis of diltiazem. Isolation of the crystalline complex from the reaction of 1 and SnCl4; and its efficient catalytic activity similar to that of SnCl4 suggests that the transition state involves co‐coordination of tin derivatives both with 1 and the epoxy oxygen of 2a to result in highly specific cis‐opening. We have also amplified this chemistry into other fields, leading to applications in the syntheses of cephem and taxoid templates. © 2000 John Wiley & Sons, Inc. Med Res Rev, 20, No. 6, 485–501, 2000

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confidence: 99%

Applications of Lewis acids for the efficient syntheses of diltiazem, cephems, and taxoids

Hashiyama

2000

Med. Res. Rev.

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“…[327] Docetaxel, a paclitaxel analogue, is accessible in a very similar way. [320,328] The drug was developed by Rhône-Poulenc-Rorer and marketed in 1995 under the name Taxotere .…”

Section: Taxolmentioning

confidence: 99%

Natural Products in the Chemical Industry

Schaefer¹

2014

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“…[324] 5.8 Taxol ® Alain Commerçon of the Rhône-Poulenc-Rorer company used (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid as a building block for the side-chain, and he likewise obtained paclitaxel, although in lower yield. [327] Docetaxel, a paclitaxel analogue, is accessible in a very similar way. [320,328] The drug was developed by Rhône-Poulenc-Rorer and marketed in 1995 under the name Taxotere ® .…”

Section: Partial Synthesismentioning

confidence: 99%

Pharmaceuticals

Schaefer

2014

Natural Products in the Chemical Industry

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A boy who is born in Germany today has a probable life expectancy of around 77 years, and a girl one of 82 years -twice as long as in the year 1880. This increase is a consequence of both, better living circumstances -working conditions, food, clothing, housing -, and also a result of more comprehensive medical care. Thus, a whole range of infectious diseases has been wiped out, or brought at least under control, and the mortality rate for civilisation-and age-related diseases has dropped. Vaccinations and drugs play a key role in this outcome. The 20th century is characterised especially by the worldwide blossoming of the pharmaceutical industry. More and more, the targeted search for and development of new drugs have replaced serendipitous discoveries (Fig. 5.1). Pharmaceuticals of the last century.

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Improved protection and esterification of a precursor of the taxotere® and taxol side chains

Cited by 128 publications

References 12 publications

Applications of Lewis acids for the efficient syntheses of diltiazem, cephems, and taxoids

Applications of Lewis acids for the efficient syntheses of diltiazem, cephems, and taxoids

Natural Products in the Chemical Industry

Pharmaceuticals

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