Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach

Hojong Yoon, Kyung Seon Cho, Taebo Sim

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

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)-α-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.

Original languageEnglish
Pages (from-to)497-502
Number of pages6
JournalTetrahedron Asymmetry
Volume25
Issue number6-7
DOIs
Publication statusPublished - 2014 Apr 15

Bibliographical note

Funding Information:
This research was supported by Korea Institute of Science and Technology and a Grant ( NRF-2011-0028676 ) from the creative/challenging research program of National Research Foundation of Korea and a Grant ( D33400 ) from Korea Basic Science Institute and a Grant ( A111345 ) from the Korea Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea .

Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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