Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines: D-glucose-derived aziridine-2-carboxylate approach

K. S.Ajish Kumar; Vinod D. Chaudhari; Vedavati G. Puranik; Dilip D. Dhavale

doi:10.1002/ejoc.200700461

Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines: D-glucose-derived aziridine-2-carboxylate approach

K. S.Ajish Kumar
, Vinod D. Chaudhari
, Vedavati G. Puranik
, Dilip D. Dhavale

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

22 Scopus citations

Abstract

D-Glucose-derived aziridine-2-carboxylate 1 was converted into α-amino aldehyde 7, which, after Wittig olefination, asymmetric dihydroxylation, hydrogenation followed by LiAlH₄ reduction, and N-Cbz protection, afforded two diastereomeric pyrrolidines 11a and 11b with sugar appendages. Removal of the 1,2-acetonide functionality in 11a/11b and reductive amination gave the pentahydroxyindolizidine alkaloids 6g and 6h, respectively, with (S) absolute configurations at the ring junctions. The glycosidase inhibitory activities of these compounds were studied.

Original language	English
Pages (from-to)	4895-4901
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	29
DOIs	https://doi.org/10.1002/ejoc.200700461
State	Published - 24 Oct 2007
Externally published	Yes

Keywords

Asymmetric dihydroxylation (AD)
Iminosugars
Indolizidine
N-methylmorpholine N-oxide (NMO)

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.200700461

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title = "Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines: D-glucose-derived aziridine-2-carboxylate approach",

abstract = "D-Glucose-derived aziridine-2-carboxylate 1 was converted into α-amino aldehyde 7, which, after Wittig olefination, asymmetric dihydroxylation, hydrogenation followed by LiAlH4 reduction, and N-Cbz protection, afforded two diastereomeric pyrrolidines 11a and 11b with sugar appendages. Removal of the 1,2-acetonide functionality in 11a/11b and reductive amination gave the pentahydroxyindolizidine alkaloids 6g and 6h, respectively, with (S) absolute configurations at the ring junctions. The glycosidase inhibitory activities of these compounds were studied.",

keywords = "Asymmetric dihydroxylation (AD), Iminosugars, Indolizidine, N-methylmorpholine N-oxide (NMO)",

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

year = "2007",

month = oct,

day = "24",

doi = "10.1002/ejoc.200700461",

language = "English",

pages = "4895--4901",

journal = "European Journal of Organic Chemistry",

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publisher = "John Wiley and Sons Ltd",

number = "29",

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TY - JOUR

T1 - Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines

T2 - D-glucose-derived aziridine-2-carboxylate approach

AU - Kumar, K. S.Ajish

AU - Chaudhari, Vinod D.

AU - Puranik, Vedavati G.

AU - Dhavale, Dilip D.

PY - 2007/10/24

Y1 - 2007/10/24

N2 - D-Glucose-derived aziridine-2-carboxylate 1 was converted into α-amino aldehyde 7, which, after Wittig olefination, asymmetric dihydroxylation, hydrogenation followed by LiAlH4 reduction, and N-Cbz protection, afforded two diastereomeric pyrrolidines 11a and 11b with sugar appendages. Removal of the 1,2-acetonide functionality in 11a/11b and reductive amination gave the pentahydroxyindolizidine alkaloids 6g and 6h, respectively, with (S) absolute configurations at the ring junctions. The glycosidase inhibitory activities of these compounds were studied.

AB - D-Glucose-derived aziridine-2-carboxylate 1 was converted into α-amino aldehyde 7, which, after Wittig olefination, asymmetric dihydroxylation, hydrogenation followed by LiAlH4 reduction, and N-Cbz protection, afforded two diastereomeric pyrrolidines 11a and 11b with sugar appendages. Removal of the 1,2-acetonide functionality in 11a/11b and reductive amination gave the pentahydroxyindolizidine alkaloids 6g and 6h, respectively, with (S) absolute configurations at the ring junctions. The glycosidase inhibitory activities of these compounds were studied.

KW - Asymmetric dihydroxylation (AD)

KW - Iminosugars

KW - Indolizidine

KW - N-methylmorpholine N-oxide (NMO)

UR - https://www.scopus.com/pages/publications/35349022564

U2 - 10.1002/ejoc.200700461

DO - 10.1002/ejoc.200700461

M3 - Article

AN - SCOPUS:35349022564

SN - 1434-193X

SP - 4895

EP - 4901

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 29

ER -

Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines: D-glucose-derived aziridine-2-carboxylate approach

Abstract

Keywords

ASJC Scopus subject areas

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