상세 보기
Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine
- Lee, Baeck Kyoung;
- Choi, Hwan Geun;
- Roh, Eun Joo;
- Lee, Won Koo;
- Sim, Taebo
Citations
WEB OF SCIENCE
17Citations
SCOPUS
19초록
An efficient synthesis of (-)-8-epi-swainsonine, starting from a commercially available 1-(R)-alpha-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-beta followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (-)-8-epi-swainsonine. (c) 2012 Elsevier Ltd. All rights reserved.
키워드
Indolizidine alkaloids; (-)-8-Epi-swainsonine; Total synthesis; Aziridine; Natural product; RING-CLOSING METATHESIS; ASYMMETRIC SYNTHESES; SWAINSONA-CANESCENS; NATURAL OCCURRENCE; ALPHA-MANNOSIDASE; (-)-SWAINSONINE; INHIBITION; ALKALOIDS; ANALOGS; DIHYDROXYLATION
- 제목
- Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine
- 저자
- Lee, Baeck Kyoung; Choi, Hwan Geun; Roh, Eun Joo; Lee, Won Koo; Sim, Taebo
- 발행일
- 2013-02-06
- 유형
- Article
- 권
- 54
- 호
- 6
- 페이지
- 553 ~ 556