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Synfacts 2014; 10(1): 0006
DOI: 10.1055/s-0033-1340325
DOI: 10.1055/s-0033-1340325
Synthesis of Natural Products and Potential Drugs
A Formal Synthesis of Atorvastatin
Further Information
Publication History
Publication Date:
13 December 2013 (online)
![](https://www.thieme-connect.de/media/synfacts/201401/i_k071_s1_10-1055_s-0033-1340325.gif)
Significance
The key step in this formal synthesis of atorvastatin (Lipitor®) is the enantioselective intramolecular oxa-Michael reaction of A mediated by 10 mol% of benzothiadiazine catalyst B. Methods for converting G and its relatives into atorvastatin have been summarized by Y. Kawato et al. (Chem. Eur. J. 2013, 19, 3802; see also references therein).
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Comment
For the conversion of N-nitrosamides into esters (e.g., D → E), see: D. T. Glatzhofer, R. R. Roy, K. N. Cossey Org. Lett. 2002, 4, 2349. Phenolic nucleophiles (14 examples) also participate in the oxa-Michael reaction, and in the case of H only 1 mol% of catalyst I is required.
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![](https://www.thieme-connect.de/media/synfacts/201401/i_k071_s1_10-1055_s-0033-1340325.gif)