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Open AccessReview

Epoxide Syntheses and Ring-Opening Reactions in Drug Development

Department of Chemistry, University of Patras, 26504 Patra, Greece
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Catalysts 2020, 10(10), 1117; https://doi.org/10.3390/catal10101117
Received: 23 August 2020 / Revised: 22 September 2020 / Accepted: 23 September 2020 / Published: 27 September 2020
(This article belongs to the Special Issue Catalytic Asymmetric Epoxidation: Recent Progress)
This review concentrates on success stories from the synthesis of approved medicines and drug candidates using epoxide chemistry in the development of robust and efficient syntheses at large scale. The focus is on those parts of each synthesis related to the substrate-controlled/diastereoselective and catalytic asymmetric synthesis of epoxide intermediates and their subsequent ring-opening reactions with various nucleophiles. These are described in the form of case studies of high profile pharmaceuticals spanning a diverse range of indications and molecular scaffolds such as heterocycles, terpenes, steroids, peptidomimetics, alkaloids and main stream small molecules. Representative examples include, but are not limited to the antihypertensive diltiazem, the antidepressant reboxetine, the HIV protease inhibitors atazanavir and indinavir, efinaconazole and related triazole antifungals, tasimelteon for sleep disorders, the anticancer agent carfilzomib, the anticoagulant rivaroxaban the antibiotic linezolid and the antiviral oseltamivir. Emphasis is given on aspects of catalytic asymmetric epoxidation employing metals with chiral ligands particularly with the Sharpless and Jacobsen–Katsuki methods as well as organocatalysts such as the chiral ketones of Shi and Yang, Pages’s chiral iminium salts and typical chiral phase transfer agents. View Full-Text
Keywords: epoxides; drug development; catalytic asymmetric epoxidation; organocatalysis; process development and manufacturing routes; Sharpless and Jacobsen–Katsuki asymmetric epoxidation; chiral ketones/dioxiranes; iminium/oxaziridinium salts; epoxide ring opening epoxides; drug development; catalytic asymmetric epoxidation; organocatalysis; process development and manufacturing routes; Sharpless and Jacobsen–Katsuki asymmetric epoxidation; chiral ketones/dioxiranes; iminium/oxaziridinium salts; epoxide ring opening
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MDPI and ACS Style

Moschona, F.; Savvopoulou, I.; Tsitopoulou, M.; Tataraki, D.; Rassias, G. Epoxide Syntheses and Ring-Opening Reactions in Drug Development. Catalysts 2020, 10, 1117.

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