Asymmetric synthesis of H-1 receptor antagonist (R,R)-clemastine
- Authors
- Lee, Sun Young; Jung, Jung Wha; Kim, Tae-Hyun; Kim, Hee-Doo
- Issue Date
- Dec-2015
- Publisher
- PHARMACEUTICAL SOC KOREA
- Keywords
- (R,R)-Clemastine; H-1 receptor antagonist; Asymmetric synthesis; Asymmetric transformation
- Citation
- ARCHIVES OF PHARMACAL RESEARCH, v.38, no.12, pp 2131 - 2136
- Pages
- 6
- Journal Title
- ARCHIVES OF PHARMACAL RESEARCH
- Volume
- 38
- Number
- 12
- Start Page
- 2131
- End Page
- 2136
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/10166
- DOI
- 10.1007/s12272-015-0641-4
- ISSN
- 0253-6269
1976-3786
- Abstract
- The first asymmetric synthesis of (R,R)-clemastine (1) has been accomplished by the coupling of (R)-tertiary alcohol 2 and (R)-chloroethylpyrrolidine 3 via O-alkylation. (R)-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral alpha-benzyloxy ketone with Grignard reagent via chelation-controlled 1,4-asymmetric induction. In the reaction, chiral benzyl group acts as a chiral auxiliary as well as a protecting group. (R)-Chloroethylpyrrolidine 3 was prepared by asymmetric transformation starting with l-homoserine lactone, in which racemization-minimized N-allylation and ring-closing metathesis were involved as key steps.
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