The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester: An efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors

Vinod D. Chaudhari; K. S.Ajish Kumar; Dilip D. Dhavale

doi:10.1016/j.tetlet.2004.09.053

The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester: An efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors

Vinod D. Chaudhari, K. S.Ajish Kumar, Dilip D. Dhavale

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

18 Scopus citations

Abstract

A short and efficient synthesis of 1,4,5-trideoxy-1,4-imino-l-xylo-hexitol 2a and 1,4,5-trideoxy-1,4-imino-d-arabino-hexitol 2b is reported using the intramolecular conjugate addition of in situ generated benzylamine to the α,β-unsaturated ester 4, derived from d-glucose, as the key step.

Original language	English
Pages (from-to)	8363-8366
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2004.09.053
State	Published - 1 Nov 2004
Externally published	Yes

Keywords

Alkaloids
Carbohydrate mimetics
Enzyme inhibitors
Pyrrolidines

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.09.053

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title = "The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester: An efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors",

abstract = "A short and efficient synthesis of 1,4,5-trideoxy-1,4-imino-l-xylo-hexitol 2a and 1,4,5-trideoxy-1,4-imino-d-arabino-hexitol 2b is reported using the intramolecular conjugate addition of in situ generated benzylamine to the α,β-unsaturated ester 4, derived from d-glucose, as the key step.",

keywords = "Alkaloids, Carbohydrate mimetics, Enzyme inhibitors, Pyrrolidines",

author = "Chaudhari, {Vinod D.} and Kumar, {K. S.Ajish} and Dhavale, {Dilip D.}",

year = "2004",

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journal = "Tetrahedron Letters",

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The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester: An efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors. / Chaudhari, Vinod D.; Kumar, K. S.Ajish; Dhavale, Dilip D.
In: Tetrahedron Letters, Vol. 45, No. 45, 01.11.2004, p. 8363-8366.

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

TY - JOUR

T1 - The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester

T2 - An efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors

AU - Chaudhari, Vinod D.

AU - Kumar, K. S.Ajish

AU - Dhavale, Dilip D.

PY - 2004/11/1

Y1 - 2004/11/1

N2 - A short and efficient synthesis of 1,4,5-trideoxy-1,4-imino-l-xylo-hexitol 2a and 1,4,5-trideoxy-1,4-imino-d-arabino-hexitol 2b is reported using the intramolecular conjugate addition of in situ generated benzylamine to the α,β-unsaturated ester 4, derived from d-glucose, as the key step.

AB - A short and efficient synthesis of 1,4,5-trideoxy-1,4-imino-l-xylo-hexitol 2a and 1,4,5-trideoxy-1,4-imino-d-arabino-hexitol 2b is reported using the intramolecular conjugate addition of in situ generated benzylamine to the α,β-unsaturated ester 4, derived from d-glucose, as the key step.

KW - Alkaloids

KW - Carbohydrate mimetics

KW - Enzyme inhibitors

KW - Pyrrolidines

UR - http://www.scopus.com/inward/record.url?scp=5444256880&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2004.09.053

DO - 10.1016/j.tetlet.2004.09.053

M3 - Article

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SN - 0040-4039

VL - 45

SP - 8363

EP - 8366

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester: An efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors

Abstract

Keywords

ASJC Scopus subject areas

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