Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

Daisuke Minehira; Takuya Okada; Ren Iwaki; Atsushi Kato; Isao Adachi; Naoki Toyooka

doi:10.1016/j.tetlet.2014.11.087

Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

Daisuke Minehira^*, Takuya Okada, Ren Iwaki, Atsushi Kato, Isao Adachi, Naoki Toyooka^*

^*Corresponding author for this work

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

4 Scopus citations

Abstract

The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1. The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l-fucosidase and a high selectivity compared from the other glycosidases.

Original language	English
Pages (from-to)	331-334
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2014.11.087
State	Published - 2015/01/08

Keywords

Enantiodivergent strategy
Glycosidase
Hyacinthacine
Imino sugar
Pyrrolizidine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.11.087

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title = "Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases",

abstract = "The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1. The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l-fucosidase and a high selectivity compared from the other glycosidases.",

keywords = "Enantiodivergent strategy, Glycosidase, Hyacinthacine, Imino sugar, Pyrrolizidine",

author = "Daisuke Minehira and Takuya Okada and Ren Iwaki and Atsushi Kato and Isao Adachi and Naoki Toyooka",

note = "Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd.",

year = "2015",

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doi = "10.1016/j.tetlet.2014.11.087",

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T1 - Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

AU - Minehira, Daisuke

AU - Okada, Takuya

AU - Iwaki, Ren

AU - Kato, Atsushi

AU - Adachi, Isao

AU - Toyooka, Naoki

PY - 2015/1/8

Y1 - 2015/1/8

N2 - The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1. The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l-fucosidase and a high selectivity compared from the other glycosidases.

AB - The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1. The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l-fucosidase and a high selectivity compared from the other glycosidases.

KW - Enantiodivergent strategy

KW - Glycosidase

KW - Hyacinthacine

KW - Imino sugar

KW - Pyrrolizidine

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U2 - 10.1016/j.tetlet.2014.11.087

DO - 10.1016/j.tetlet.2014.11.087

M3 - 学術論文

AN - SCOPUS:84922261762

SN - 0040-4039

VL - 56

SP - 331

EP - 334

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

Abstract

Keywords

ASJC Scopus subject areas

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