Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine

Baeck Kyoung Lee, Hwan Geun Choi, Eun Joo Roh, Won Koo Lee, Taebo Sim

Research output: Contribution to journalArticle

13 Citations (Scopus)

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 languageEnglish
Pages (from-to)553-556
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number6
DOIs
Publication statusPublished - 2013 Feb 6

Fingerprint

Cyclization
Allylation
Methanol
8-epi-swainsonine
aziridine
piperidine

Keywords

  • (-)-8-Epi-swainsonine
  • Aziridine
  • Indolizidine alkaloids
  • Natural product
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine. / Lee, Baeck Kyoung; Choi, Hwan Geun; Roh, Eun Joo; Lee, Won Koo; Sim, Taebo.

In: Tetrahedron Letters, Vol. 54, No. 6, 06.02.2013, p. 553-556.

Research output: Contribution to journalArticle

Lee, Baeck Kyoung ; Choi, Hwan Geun ; Roh, Eun Joo ; Lee, Won Koo ; Sim, Taebo. / Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine. In: Tetrahedron Letters. 2013 ; Vol. 54, No. 6. pp. 553-556.
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