An Efficient Semi‐Synthetic Method to Construct Docetaxel via Sterically Crowded Linear Side Chain Esterification

Shen, Xiaotao; Yang, Jun; Zhan, Huaxing; Wang, Hu; Wu, Shaohong; Chen, Zili

doi:10.1002/cjoc.201201142

Cited by 5 publications

(3 citation statements)

References 39 publications

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“…First, to confirm that the hydroxy group introduced in this reaction originated from O 2 , we performed the cyclization reaction without the reductive workup step, resulting in hyroperoxide 2′ in 59% yield (reaction (1)). 25 This result clearly indicates that the Mn(acac) 3 -catalyzed reaction proceeded via hydroperoxidation of the α,β-unsaturated alkene by using O 2 present in the air instead of epoxidation of the alkene and the subsequent epoxide opening reaction. To prove the necessity of O 2 , this Mn(acac) 3 -catalyzed reaction was attempted under an Ar atmosphere, resulting in the quantitative recovery of the starting material 3g (reaction (2)).…”

Section: ■ Results and Discussionmentioning

confidence: 87%

Manganese-Catalyzed 5-Endo-trig Oxygenative Cyclization of α,β-Unsaturated Oximes under Air and Ambient Conditions for the Synthesis of 4,5-Dihydroisoxazoles

Yamamoto,

Matsukawa,

Kikuchi

et al. 2024

J. Org. Chem.

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The stereoselective 5-endo-trig oxygenative cyclization of α,β-unsaturated oximes was achieved using molecular oxygen (O 2 ) and a manganese catalyst. Several 4-hydroxy-4,5dihydroisoxazoles were obtained in high yields by directly incorporating O 2 from the atmosphere (eliminating the necessity for a pure oxygen environment) and using an unprecedentedly low loading of Mn(acac) 3 (as little as 0.020 mol %) without additional additives. Because of its desirable features, such as operational simplicity, inexpensive catalyst, mild reaction conditions (open flask conditions at room temperature), and broad substrate compatibility, this novel reaction provides an attractive synthetic approach to producing 4-hydroxy-4,5-dihydroisoxazoles.

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Section: ■ Results and Discussionmentioning

confidence: 87%

Manganese-Catalyzed 5-Endo-trig Oxygenative Cyclization of α,β-Unsaturated Oximes under Air and Ambient Conditions for the Synthesis of 4,5-Dihydroisoxazoles

Yamamoto,

Matsukawa,

Kikuchi

et al. 2024

J. Org. Chem.

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“…Many research groups have done studies of DTX, including the structure, function, docking mechanism, and clinical trials to understand the action of DTX on its microtubule target. These studies have highlighted the relevance of the amino acidic side chain at C13 (see green dot, Fig.…”

Section: Introductionmentioning

confidence: 99%

Conformers, properties, and docking mechanism of the anticancer drug docetaxel: DFT and molecular dynamics studies

et al. 2018

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The conformational structures and properties of the anticancer drug docetaxel (DTX) are studied theoretically. A total of 3888 trial structures were initially generated by all combinations of internal single-bond rotamers and screened with the B3LYP/3-21G* method. A total of 31 unique conformers were further optimized at the B3LYP/6-311G* method. Their relative energies, dipole moments, rotational constants, and harmonic vibrational frequencies were predicted. Single-point relative energies were then determined at the M06-L/6-311G(2df,p) level. The UV spectrum of the lowest-lying DTX conformer in methanol was investigated with the TD-CAM-B3LYP/6-311 + G(2df,p) method. The 31 unique DTX structures are mainly docked at three different sites within β-tubulin. Based on the results of molecular docking and double-float MD simulations, the lowest-lying DTX conformer consistently exhibits good docking performance with β-tubulin. We identified the residues LYS299, ARG215, GLN294, LEU275, THR216, GLU290, PRO274, and THR276 on β-tubulin as active sites forming a binding pocket responsible for locking DTX within β-tubulin to make the combination more stable. The RMSD values show that the predicted complexes are favorable, and the SASA analysis shows that the hydrophilic properties of DTX are better than paclitaxel. © 2018 Wiley Periodicals, Inc.

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“…The cyclic sulfamidates 7 produced in these reactions are valuable intermediates for the synthesis of various chiral b-amino-ahydroxy carboxylic acids or 1,2-functionalized amines 16 such as those present in the side chain of the anticancer drug taxotere (10) 17 and the potent cytokine modulator (À)-epi-cytoxazone (12) 2b,18 (Fig. 1).…”

mentioning

confidence: 99%

Stereoselective synthesis of 4-substituted-cyclic sulfamidate-5-carboxylates by asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution and applications to concise stereoselective syntheses of (−)-epi-cytoxazone and the taxotere side-chain

et al. 2014

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An Efficient Semi‐Synthetic Method to Construct Docetaxel via Sterically Crowded Linear Side Chain Esterification

Cited by 5 publications

References 39 publications

Manganese-Catalyzed 5-Endo-trig Oxygenative Cyclization of α,β-Unsaturated Oximes under Air and Ambient Conditions for the Synthesis of 4,5-Dihydroisoxazoles

Manganese-Catalyzed 5-Endo-trig Oxygenative Cyclization of α,β-Unsaturated Oximes under Air and Ambient Conditions for the Synthesis of 4,5-Dihydroisoxazoles

Conformers, properties, and docking mechanism of the anticancer drug docetaxel: DFT and molecular dynamics studies

Stereoselective synthesis of 4-substituted-cyclic sulfamidate-5-carboxylates by asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution and applications to concise stereoselective syntheses of (−)-epi-cytoxazone and the taxotere side-chain

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