Substrate stereocontrol in bromine-induced intermolecular cyclization: asymmetric synthesis of pitavastatin calcium

Chen, Weiqi; Xiong, Fei; Liu, Qian; Xu, Lizhe; Wu, Yan; Chen, Fen‐Er

doi:10.1016/j.tet.2015.05.053

Cited by 9 publications

(14 citation statements)

References 47 publications

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“…Biocatalyzed approach to the C-7 chiral atorvastatin lateral-chain precursor using E. coli cells expressing KR and GDH for a cofactor regeneration 134 Z. Č asar conditions, 80.0 g/L loading of t-butyl 6-cyano-(5R)-hydroxy-3-oxohexanoate 68 was fully converted to t-butyl 6-cyano-(3R,5R)-dihydroxylhexanoate 69 in 2 h, with de > 99.5%. Kawato et al [97] also upgraded their primary approach to the C-7 chiral atorvastatin lateral-chain precursor.…”

Section: Scheme 11mentioning

confidence: 99%

“…The Wittig reaction of the aldehyde 123 and the ylide, which was derived from the salt 229h with K 2 CO 3 base in DMSO at 70 C, provided the acetonide-protected pitavastatin methyl ester 252 at 72% yield. A removal of the acetonide-protecting group with HCl in MeCN at 45 C, followed by the hydrolysis of the ester moiety with NaOH at room temperature and the cation exchange with CaCl 2 , provided pitavastatin calcium 244 at 85% yield over three steps [134]. Statins, and in particular the super-statins, continue to inspire and attract synthetic chemists for the development of new approaches for their efficient preparation.…”

Section: Assembly Of Pitavastatinmentioning

confidence: 99%

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Synthesis of Heterocycles in Contemporary Medicinal Chemistry

Časar¹

2016

Topics in Heterocyclic Chemistry

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The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community.The series consists of topic related volumes edited by renowned editors with contributions of experts in the field.More information about this series at

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Section: Scheme 11mentioning

confidence: 99%

Section: Assembly Of Pitavastatinmentioning

confidence: 99%

Synthesis of Heterocycles in Contemporary Medicinal Chemistry

Časar¹

2016

Topics in Heterocyclic Chemistry

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“…Very recently, Chen et al [134] described the synthesis of the pitavastatin quinoline derivative 229h that contains the triphenylphosphonium tetrafluoroborate salt moiety (Scheme 49). This synthesis started with the cyclopropyl methyl ketone 236, which was reacted at 0 C with NaH in THF to provide the corresponding enolate, which was reacted with ethyl formate to provide the isolatable sodium enolate 237 at 88% yield.…”

Section: Synthesis Of the Pitavastatin Quinoline Heterocyclic Corementioning

confidence: 99%

“…Chen et al [134] described the synthesis of pitavastatin using the Wittig reaction between the triphenylphosphonium tetrafluoroborate salt 229h and the aldehydetype dually protected C-6 lateral-chain precursor 123 (Scheme 53). The 123 was prepared starting from (R)-3-chloro-1,2-propanediol 250, via the homoallylic carbonate 251 in a total of 10 steps.…”

Section: Assembly Of Pitavastatinmentioning

confidence: 99%

Section: Assembly Of Pitavastatinmentioning

confidence: 99%

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Recent Progress in the Synthesis of Super-Statins

Časar

2015

Topics in Heterocyclic Chemistry

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Super-statins now represent a mature class of marketed drugs that faces the patent cliff, as has already occurred for fluvastatin and atorvastatin and is approaching for rosuvastatin and pitavastatin. However, they continue to trigger huge scientific interest in terms of their efficient preparation. This is not surprising, as easier accessibility of super-statins will promote even bigger demand in the market and consequently the need for higher rates of the production and productivity. Therefore, the stimulus for the development of even more efficient synthetic approaches to the heterocyclic moieties of super-statins and their chiral lateralchain precursors is at a peak, as also for the assembly of the these two parts into super-statins. The present report summarizes recent developments in the field of the synthesis of super-statins published from 2010 to 2015. Emphasis is given to the analysis of novel approaches to the formation of the chiral statin lateral chain, with detailed discussion of the development of new routes to respective heterocyclic cores and the assembly of these key units into the final super-statin structure.

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Asymmetric Synthesis of Atorvastatin Calcium through Intramolecular Oxidative Oxygen‐Nucleophilic Bromocyclization

Liu

Huang

et al. 2017

Eur J Org Chem

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The stereocontrolled synthesis of atorvastatin calcium starting from commercially available d‐aspartic acid using an intramolecular oxidative oxygen‐nucleophilic bromocyclization of a homoallylic tert‐butyl carbonate is described. This strategy allows the formation of the chiral syn‐1,3‐diol moiety with the desired stereochemistry, and provides a functionalized bromomethyl group for the construction of the atorvastatin side‐chain with high regio‐ and diastereoselectivity. This route is attractive as it represents an efficient and environmentally sensitive approach to the large‐scale synthesis of statins and their analogues.

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Substrate stereocontrol in bromine-induced intermolecular cyclization: asymmetric synthesis of pitavastatin calcium

Cited by 9 publications

References 47 publications

Synthesis of Heterocycles in Contemporary Medicinal Chemistry

Synthesis of Heterocycles in Contemporary Medicinal Chemistry

Recent Progress in the Synthesis of Super-Statins

Asymmetric Synthesis of Atorvastatin Calcium through Intramolecular Oxidative Oxygen‐Nucleophilic Bromocyclization

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