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

Hojong Yoon, Kyung Seon Cho, Taebo Sim

Research output: Contribution to journalArticle

12 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

Fingerprint

Alkaloids
alkaloids
Methanol
Indolizidines
methyl alcohol
routes
Pyrrolidinones
expansion
rings
synthesis
lentiginosine
aziridine
pyrrolidine

ASJC Scopus subject areas

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

Cite this

Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach. / Yoon, Hojong; Cho, Kyung Seon; Sim, Taebo.

In: Tetrahedron Asymmetry, Vol. 25, No. 6-7, 15.04.2014, p. 497-502.

Research output: Contribution to journalArticle

Yoon, Hojong ; Cho, Kyung Seon ; Sim, Taebo. / Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach. In: Tetrahedron Asymmetry. 2014 ; Vol. 25, No. 6-7. pp. 497-502.
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