상세 보기
Efficient strategy for the stereoselective synthesis of 2,3-disubstituted benzo[alpha]quinolizidine alkaloids: concise synthesis of (-)-protoemetinol
- Moon, Hyunyoung;
- An, Hongchan;
- Sim, Jaehoon;
- Kim, Kyeojin;
- Paek, Seung-Mann;
- 외 1명
Citations
WEB OF SCIENCE
11Citations
SCOPUS
13초록
The stereoselective synthesis of (-)-protoemetinol has been accomplished through nine steps from a known homoallylic amine. The key steps of the synthesis involve the efficient preparation of an aza-Claisen rearrangement (ACR) precursor using cross metathesis and amide enolate-induced ACR followed by acid-catalyzed transannulation for the elaboration of the benzo[alpha]quinolizine skeleton and three stereogenic centers. This unique synthetic route envisages a unified and versatile strategy for the synthesis of 2,3-disubstituted benzo[alpha]quinolizidine. (C) 2014 Elsevier Ltd. All rights reserved.
키워드
(-)-Protoemetinol; Benzo[alpha]quinolizidine alkaloid; Cross metathesis; Aza-Claisen rearrangement; Transannulation; ASYMMETRIC TOTAL-SYNTHESIS; CLAISEN REARRANGEMENT; PROTEIN-SYNTHESIS; IPECAC ALKALOIDS; IN-VITRO; EMETINE; ISOMERIZATION; TETRABENAZINE; (+/-)-EMETINE; TUBULOSINE
- 제목
- Efficient strategy for the stereoselective synthesis of 2,3-disubstituted benzo[alpha]quinolizidine alkaloids: concise synthesis of (-)-protoemetinol
- 저자
- Moon, Hyunyoung; An, Hongchan; Sim, Jaehoon; Kim, Kyeojin; Paek, Seung-Mann; Suh, Young-Ger
- 발행일
- 2015-01-21
- 유형
- Article
- 권
- 56
- 호
- 4
- 페이지
- 608 ~ 611