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

doi:10.1016/j.tetlet.2013.08.040

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 journal › Article › peer-review

12 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 language	English
Pages (from-to)	5775-5777
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2013.08.040
Publication status	Published - 2013 Oct 23

Bibliographical note

Funding Information:
This research was supported by Korea Institute of Science and Technology and a grant ( 2011-0028676 ) from the creative/challenging research program of National Research Foundation of Korea funded by the Ministry of Education, Science and Technology .

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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, Efficient synthesis, Natural product, d-AB1/l-AB1, d-DIX/l-DIX",

author = "Choi, {Hwan Geun} and Park, {Dong Sik} and Lee, {Won Koo} and Taebo Sim",

note = "Funding Information: This research was supported by Korea Institute of Science and Technology and a grant ( 2011-0028676 ) from the creative/challenging research program of National Research Foundation of Korea funded by the Ministry of Education, Science and Technology . ",

year = "2013",

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doi = "10.1016/j.tetlet.2013.08.040",

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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

N1 - Funding Information: This research was supported by Korea Institute of Science and Technology and a grant ( 2011-0028676 ) from the creative/challenging research program of National Research Foundation of Korea funded by the Ministry of Education, Science and Technology .

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 - Efficient synthesis

KW - Natural product

KW - d-AB1/l-AB1

KW - d-DIX/l-DIX

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DO - 10.1016/j.tetlet.2013.08.040

M3 - Article

AN - SCOPUS:84884290031

SN - 0040-4039

VL - 54

SP - 5775

EP - 5777

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

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

Bibliographical note

Keywords

ASJC Scopus subject areas

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