An improved synthesis of 1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a key intermediate for atorvastatin synthesis

Rádl, S.; Stach, Jan; Hájíček, Josef

doi:10.1016/s0040-4039(02)00175-2

Cited by 29 publications

(14 citation statements)

References 18 publications

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“…It also has relatively low yields in some of the final stages for final purification, but this pathway has a high potential for large scale and high Kg and requires little improvement. For this reason, the Holland Group had to adopt a different approach [33]. One of the major components of this effort was a broad study of the Paal-knorr condensation by Alan Miller at the Chemical Development Company, which successfully applied a cyclodehydration to the model system when using a full eq pioalic acid as a catalyst (Scheme 10).…”

Section: Preparation Of Atorvastatinmentioning

confidence: 99%

A Review on Synthesis and Applications of Statin Family Drugs as a New Generations of Anti-Blood Medicines

2020

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Cardiovascular disease (CVD) represents one of the most important health problems. One of the main risk factors for CVD death is the high cholesterol levels. Statins have been shown to lower low-density lipoprotein (LDL) cholesterol levels and the risk of cardiovascular disease, and are currently the first line of treatment for hypercholesterolemia. Atorvastatin is one of the most effective drugs and is part of the blood lipid lowering drug group. This work studies the mechanism of the use of statin family drugs and atorvastatin to determine the clinical requirements for improving the dermatology and the statins.

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Section: Preparation Of Atorvastatinmentioning

confidence: 99%

A Review on Synthesis and Applications of Statin Family Drugs as a New Generations of Anti-Blood Medicines

2020

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“…To overcome this problem we studied the influence of AcONa on the catalytic performance of Ru[(R)-BINAP]Cl 2 (runs [19][20]. It is interesting to note that AcONa acted in the same way as Et 3 N, for example, lowering the activity with an increase in the AcONa/Ru ratio and complete inhibition of the hydrogenation at a ratio of 2 (runs [19][20] To optimize the substrate to catalyst ratio, several Ru(II) precatalysts, additives, solvents, and conditions (like, temperature and initial H 2 -pressure) have been tested. Finally, the best results were achieved with Ru[(R)-Tol-BINAP]Cl 2 3 AcONa in EtOH at 508C and 100 bar initial H 2 -pressure.…”

Section: Synthesis Of Atorvastatinmentioning

confidence: 99%

Highly stereoselective hydrogenations—As key‐steps in the total synthesis of statins

Andrushko

Tararov

et al. 2009

Chirality

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Statins are inhibitors of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase (HMG-CoA reductase) and became the standard of care for treatment of hypercholesterolemia because of their efficacy, safety, and long-term benefits. They are administered as diastereo- and enantiomerically pure compounds. We summarize here two new approaches for the total synthesis of the most important representatives, atorvastatin, and rosuvastatin, based on highly stereoselective hydrogenations as key-steps.

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“…A few recent examples are: the synthesis of the piperidine alkaloids lobelin, sedamine [85] and allosedamine [86]; and the dihydroxy carboxylate atorvastatin [87], a synthetic lipid-lowering agent of great medicinal and commercial importance.…”

Section: Intramolecular Coiodination Of Alkenes With Other Oxygenatedmentioning

confidence: 99%

A Centennial Methodology for the Preparation of Heterocyclic Compounds: The Intramolecular Coiodination of Alkenes with Internal Oxygenated Nucleophiles

Silva¹,

Jones²,

Mattos³

2005

COS

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A review on the intramolecular coiodination of alkenes with internal oxygenated nucleophiles (alkenols, unsaturated ethers, carboxylic acids and derivatives) is presented. The reactions are discussed with emphasis in the preparation of iodotetrahydrofurans, iodotetrahydropyrans and iodolactones and their utilization in organic synthesis. The intramolecular coiodination of alkenes with less common oxygenated nucleophiles (unsaturated carbonates, phosphates, isoxazolines, uretanes, hydroperoxides and silenols) is also presented. da Silva et al.Recently, we reported the intermolecular coiodination of alkenes with oxygenated nucleophiles [17], and the products (iodohydrins, β-iodoethers and β-iodoesters) proved to be

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An improved synthesis of 1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a key intermediate for atorvastatin synthesis

Cited by 29 publications

References 18 publications

A Review on Synthesis and Applications of Statin Family Drugs as a New Generations of Anti-Blood Medicines

A Review on Synthesis and Applications of Statin Family Drugs as a New Generations of Anti-Blood Medicines

Highly stereoselective hydrogenations—As key‐steps in the total synthesis of statins

A Centennial Methodology for the Preparation of Heterocyclic Compounds: The Intramolecular Coiodination of Alkenes with Internal Oxygenated Nucleophiles

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