Stereocontrolled total synthesis of (+)-1-deoxynojirimycin

Gregory Danoun; Julien Ceccon; Andrew E. Greene; Jean François Poisson

doi:10.1002/ejoc.200900595

Stereocontrolled total synthesis of (+)-1-deoxynojirimycin

Gregory Danoun
, Julien Ceccon
, Andrew E. Greene
, Jean François Poisson

LTHE (UMR 5564 CNRS/IRD/Université de Grenoble)

Research output: Contribution to journal › Article › peer-review

Abstract

A highly efficient non-chiral-pool synthesis of (+)-1-deoxynojirimycin has been realized (24% overall yield, 11 steps, complete stereocontrol). A novel one-pot enol ether metathesis/hydroboration/oxidation sequence is used for the selective formation of the all-trans cyclic triol.

Original language	English
Pages (from-to)	4221-4224
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.200900595
Publication status	Published - 1 Jan 2009
Externally published	Yes

Keywords

Azasugars
Metathesis
Natural products
Synthetic methods
Total synthesis

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10.1002/ejoc.200900595

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title = "Stereocontrolled total synthesis of (+)-1-deoxynojirimycin",

abstract = "A highly efficient non-chiral-pool synthesis of (+)-1-deoxynojirimycin has been realized (24\% overall yield, 11 steps, complete stereocontrol). A novel one-pot enol ether metathesis/hydroboration/oxidation sequence is used for the selective formation of the all-trans cyclic triol.",

keywords = "Azasugars, Metathesis, Natural products, Synthetic methods, Total synthesis",

author = "Gregory Danoun and Julien Ceccon and Greene, \{Andrew E.\} and Poisson, \{Jean Fran{\c c}ois\}",

year = "2009",

month = jan,

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doi = "10.1002/ejoc.200900595",

language = "English",

pages = "4221--4224",

journal = "European Journal of Organic Chemistry",

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AU - Danoun, Gregory

AU - Ceccon, Julien

AU - Greene, Andrew E.

AU - Poisson, Jean François

PY - 2009/1/1

Y1 - 2009/1/1

N2 - A highly efficient non-chiral-pool synthesis of (+)-1-deoxynojirimycin has been realized (24% overall yield, 11 steps, complete stereocontrol). A novel one-pot enol ether metathesis/hydroboration/oxidation sequence is used for the selective formation of the all-trans cyclic triol.

AB - A highly efficient non-chiral-pool synthesis of (+)-1-deoxynojirimycin has been realized (24% overall yield, 11 steps, complete stereocontrol). A novel one-pot enol ether metathesis/hydroboration/oxidation sequence is used for the selective formation of the all-trans cyclic triol.

KW - Azasugars

KW - Metathesis

KW - Natural products

KW - Synthetic methods

KW - Total synthesis

U2 - 10.1002/ejoc.200900595

DO - 10.1002/ejoc.200900595

M3 - Article

AN - SCOPUS:68949124921

SN - 1434-193X

SP - 4221

EP - 4224

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

Stereocontrolled total synthesis of (+)-1-deoxynojirimycin

Abstract

Keywords

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