An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines

Hwan Geun Choi, Dong Sik Park, Won Koo Lee, Taebo Sim

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol (d-AB1, 1 and l-AB1, 3) and 1,4-dideoxy-1,4-imino-d- and l-xylitol (d-DIX, 2 and l-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the routes more amenable to large-scale synthesis.

Original languageEnglish
Pages (from-to)5775-5777
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number43
DOIs
Publication statusPublished - 2013 Oct 23

Fingerprint

Aziridines
Xylitol
Carbon
aziridine

Keywords

  • Chiral aziridines
  • d-AB1/l-AB1
  • d-DIX/l-DIX
  • Efficient synthesis
  • Natural product

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines. / Choi, Hwan Geun; Park, Dong Sik; Lee, Won Koo; Sim, Taebo.

In: Tetrahedron Letters, Vol. 54, No. 43, 23.10.2013, p. 5775-5777.

Research output: Contribution to journalArticle

Choi, Hwan Geun ; Park, Dong Sik ; Lee, Won Koo ; Sim, Taebo. / An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines. In: Tetrahedron Letters. 2013 ; Vol. 54, No. 43. pp. 5775-5777.
@article{492b724d3b8f4c6e81fa877a49fd95ef,
title = "An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines",
abstract = "A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol (d-AB1, 1 and l-AB1, 3) and 1,4-dideoxy-1,4-imino-d- and l-xylitol (d-DIX, 2 and l-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the routes more amenable to large-scale synthesis.",
keywords = "Chiral aziridines, d-AB1/l-AB1, d-DIX/l-DIX, Efficient synthesis, Natural product",
author = "Choi, {Hwan Geun} and Park, {Dong Sik} and Lee, {Won Koo} and Taebo Sim",
year = "2013",
month = "10",
day = "23",
doi = "10.1016/j.tetlet.2013.08.040",
language = "English",
volume = "54",
pages = "5775--5777",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "43",

}

TY - JOUR

T1 - An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines

AU - Choi, Hwan Geun

AU - Park, Dong Sik

AU - Lee, Won Koo

AU - Sim, Taebo

PY - 2013/10/23

Y1 - 2013/10/23

N2 - A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol (d-AB1, 1 and l-AB1, 3) and 1,4-dideoxy-1,4-imino-d- and l-xylitol (d-DIX, 2 and l-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the routes more amenable to large-scale synthesis.

AB - A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol (d-AB1, 1 and l-AB1, 3) and 1,4-dideoxy-1,4-imino-d- and l-xylitol (d-DIX, 2 and l-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the routes more amenable to large-scale synthesis.

KW - Chiral aziridines

KW - d-AB1/l-AB1

KW - d-DIX/l-DIX

KW - Efficient synthesis

KW - Natural product

UR - http://www.scopus.com/inward/record.url?scp=84884290031&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84884290031&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.08.040

DO - 10.1016/j.tetlet.2013.08.040

M3 - Article

AN - SCOPUS:84884290031

VL - 54

SP - 5775

EP - 5777

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 43

ER -