An efficient, cyanide free total synthesis of rosuvastatin calcium
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 industria...
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| Published in: | Tetrahedron Vol. 111; p. 132717 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
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09-04-2022
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| Abstract | 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. |
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| AbstractList | 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.
[Display omitted]
•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. |
| ArticleNumber | 132717 |
| Author | Vempala, Naresh Rao, S. Venkateswara Shree, A. Jaya Matta, Balaji Maddirala, Shambabu Joseph |
| Author_xml | – sequence: 1 givenname: Naresh surname: Vempala fullname: Vempala, Naresh email: naresh_vempala@yahoo.com organization: Aragen Life Sciences, Number 12, Plot No 28 A, IDA, Nacharam, Hyderabad, Telangana, 500076, India – sequence: 2 givenname: Balaji surname: Matta fullname: Matta, Balaji organization: Centre for Chemical Sciences and Technology, Institute of Science and Technology, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad, 500085, India – sequence: 3 givenname: S. Venkateswara surname: Rao fullname: Rao, S. Venkateswara organization: Centre for Chemical Sciences and Technology, Institute of Science and Technology, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad, 500085, India – sequence: 4 givenname: Shambabu Joseph surname: Maddirala fullname: Maddirala, Shambabu Joseph organization: Aragen Life Sciences, Number 12, Plot No 28 A, IDA, Nacharam, Hyderabad, Telangana, 500076, India – sequence: 5 givenname: A. Jaya surname: Shree fullname: Shree, A. Jaya email: jayashree@jntuh.ac.in organization: Centre for Chemical Sciences and Technology, Institute of Science and Technology, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad, 500085, India |
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| Keywords | Rosuvastatin calcium Wittig reaction Oxa-michael addition Total synthesis Statins |
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