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  • 02월 19일 10시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제121회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Asymmetric Synthesis of H1 Receptor Antagonist (R,R)-Clemastine

등록일
2018년 2월 13일 11시 08분 55초
접수번호
5952
발표코드
ORGN.P-548 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
4월 19일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
Organic Chemistry
저자 및
공동저자
Hee-Doo Kim*, Sun Young Lee
College of Pharmacy, Sookmyung Women's University, Korea

Clemastine (1) is an H1-receptor antagonist with excellent antihistaminic activity. Clemastine has two chiral centers, and is marketed as the (R, R)-enantiomer. These chiralities have a significant influence on potency. However, asymmetric synthesis of (R,R)-clemastine has not been reported to date. The first asymmetric synthesis of (R,R)-clemastine (1) has been accomplished by coupling of (R)-tertiary alcohol 2 and (R)-chloroethylpyrrolidine 3 via O-alkylation. (R)-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral a-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 from L-homoserine lactone, in which racemization-minimized N-allylation and ring-closing metathesis were involved as key steps.


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