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Literature DB >> 14986985

Synthesis of the new mannosidase inhibitors, diversity-oriented 5-substituted swainsonine analogues, via stereoselective Mannich reaction.

Tomoya Fujita¹, Hideko Nagasawa, Yoshihiro Uto, Toshihiro Hashimoto, Yoshinori Asakawa, Hitoshi Hori.

Abstract

5alpha-substituted swainsonine analogues were synthesized by Mannich reaction of an in situ generated (-)-swainsonine iminium ion intermediate. 5alpha-substituted swainsonine analogues were epimerized to their 5beta-isomers in protic solvent. [reaction: see text]

Entities: Chemical

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Year: 2004 PMID： 14986985 DOI： 10.1021/ol049947m

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

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Journal: Chemistry Date: 2016-11-09 Impact factor: 5.236

Review 2. Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions.

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Journal: Ultrason Sonochem Date: 2021-08-05 Impact factor: 7.491

3. Harnessing natural-product-inspired combinatorial chemistry and computation-guided synthesis to develop N-glycan modulators as anticancer agents.

Authors: Wei-An Chen; Yu-Hsin Chen; Chiao-Yun Hsieh; Pi-Fang Hung; Chiao-Wen Chen; Chien-Hung Chen; Jung-Lee Lin; Ting-Jen R Cheng; Tsui-Ling Hsu; Ying-Ta Wu; Chia-Ning Shen; Wei-Chieh Cheng
Journal: Chem Sci Date: 2022-04-19 Impact factor: 9.969

Synthesis of the new mannosidase inhibitors, diversity-oriented 5-substituted swainsonine analogues, via stereoselective Mannich reaction.

1. Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

Review 2. Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions.

3. Harnessing natural-product-inspired combinatorial chemistry and computation-guided synthesis to develop N-glycan modulators as anticancer agents.

4. Human lysosomal alpha-mannosidases exhibit different inhibition and metal binding properties.

5. N-Benzyl Substitution of Polyhydroxypyrrolidines: The Way to Selective Inhibitors of Golgi α-Mannosidase II.

6. (7R,8R,8aS)-8-Hydr-oxy-7-phenyl-per-hydro-indolizin-3-one.