Lee, Baeck Kyoung Choi, Hwan Geun Roh, Eun Joo Lee, Won Koo Sim, Taebo 2024-01-20T13:01:49Z 2024-01-20T13:01:49Z 2021-09-01 2013-02-06 0040-4039 https://pubs.kist.re.kr/handle/201004/128361 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. English PERGAMON-ELSEVIER SCIENCE LTD RING-CLOSING METATHESIS ASYMMETRIC SYNTHESES SWAINSONA-CANESCENS NATURAL OCCURRENCE ALPHA-MANNOSIDASE (-)-SWAINSONINE INHIBITION ALKALOIDS ANALOGS DIHYDROXYLATION Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine Article 10.1016/j.tetlet.2012.11.087 1 TETRAHEDRON LETTERS, v.54, no.6, pp.553 - 556 TETRAHEDRON LETTERS 54 6 553 556 scie scopus 000314388300026 2-s2.0-84872018243 Chemistry, Organic Chemistry Article RING-CLOSING METATHESIS ASYMMETRIC SYNTHESES SWAINSONA-CANESCENS NATURAL OCCURRENCE ALPHA-MANNOSIDASE (-)-SWAINSONINE INHIBITION ALKALOIDS ANALOGS DIHYDROXYLATION Indolizidine alkaloids (-)-8-Epi-swainsonine Total synthesis Aziridine Natural product