Abstract
An efficient synthesis of (-)-8-epi-swainsonine, starting from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-β 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.
Original language | English |
---|---|
Pages (from-to) | 553-556 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 54 |
Issue number | 6 |
DOIs | |
Publication status | Published - 2013 Feb 6 |
Bibliographical note
Funding Information:This research was supported by the Korea Institute of Science and Technology and a Grant (No. 2011-0028676 ) from the creative/challenging research program of the National Research Foundation of Korea funded by the Ministry of Education, Science and Technology , and a Grant (No.: A111345 ) of the Korea Health technology R&D Project, Ministry of Health & Welfare, Republic of Korea.
Keywords
- (-)-8-Epi-swainsonine
- Aziridine
- Indolizidine alkaloids
- Natural product
- Total synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry