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 journalArticlepeer-review

18 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

Bibliographical note

Funding Information:
This research was supported by the Korea Institute of Science and Technology and a Grant (No. 2011-0028676 ) from the creative/challenging research program of the National Research Foundation of Korea funded by the Ministry of Education, Science and Technology , and a Grant (No.: A111345 ) of the Korea Health technology R&D Project, Ministry of Health & Welfare, Republic of Korea.

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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