An efficient, cyanide free total synthesis of rosuvastatin calcium

• Published in: Tetrahedron Vol. 111; p. 132717
• Main Authors: Vempala, Naresh, Matta, Balaji, Rao, S. Venkateswara, Maddirala, Shambabu Joseph, Shree, A. Jaya
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 09-04-2022
• Subjects: Oxa-michael addition; Rosuvastatin calcium; Statins; Total synthesis; Wittig reaction; Rosuvastatin calcium; Wittig reaction; Oxa-michael addition; Total synthesis; Statins
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2022.132717

A simple, efficient, cyanide-free protocol for the total synthesis of rosuvastatin calcium was developed from inexpensive, commercially available d-arabinose; the key steps employed were Wittig reaction followed by oxa-Michael addition. The developed synthetic protocol could be adopted for industrial production of rosuvastatin calcium.
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•The efficient total synthesis of rosuvastatin calcium was achieved in 22 steps without using Narasaka reduction and hazardous reagents like sodium cyanide.•The total synthesis of rosuvastatin calcium was accomplished utilising commercially available d-Arabinose and cost effective mild regents.•The key steps employed in the synthesis of the aliphatic syn diol ester were the Wittig reaction followed by the oxa-Michael addition.•Both fragments, pyridinium Wittig ylide and aliphatic aldehyde were coupled under the Wittig olefination .•The developed synthetic protocol could be adopted for industrial production of rosuvastatin calcium.