Yoon, Hojong Cho, Kyung Seon Sim, Taebo 2024-01-20T10:01:47Z 2024-01-20T10:01:47Z 2021-09-04 2014-04-15 0957-4166 https://pubs.kist.re.kr/handle/201004/126879 The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-enoate, which was prepared from commercially available 1-(S)-alpha-methylbenzylaziridine-2-methanol. In addition, a regioselective aziridine-to-pyrrolidinone ring expansion process followed by a Wittig olefination was employed to construct a late stage pyrrolidine intermediate that was transformed into (+)-lentiginosine. (c) 2014 Elsevier Ltd. All rights reserved. English PERGAMON-ELSEVIER SCIENCE LTD CONCISE TOTAL-SYNTHESIS DIRECTED DIHYDROXYLATION STEREOSELECTIVE-SYNTHESIS ALLYLIC ALCOHOLS POLYHYDROXYLATED ALKALOIDS ABSOLUTE-CONFIGURATION LENTIGINOSINE INHIBITORS TRICHLOROACETAMIDES (-)-LENTIGINOSINE Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach Article 10.1016/j.tetasy.2014.02.009 1 TETRAHEDRON-ASYMMETRY, v.25, no.6-7, pp.497 - 502 TETRAHEDRON-ASYMMETRY 25 6-7 497 502 scie scopus 000335628100004 2-s2.0-84898852140 Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry, Physical Chemistry Article CONCISE TOTAL-SYNTHESIS DIRECTED DIHYDROXYLATION STEREOSELECTIVE-SYNTHESIS ALLYLIC ALCOHOLS POLYHYDROXYLATED ALKALOIDS ABSOLUTE-CONFIGURATION LENTIGINOSINE INHIBITORS TRICHLOROACETAMIDES (-)-LENTIGINOSINE (+)-lentiginosine 천연물 전합성