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Literature DB >> 19530721

Concise synthesis of iminocyclitols via Petasis-type aminocyclization.

Zhangyong Hong¹, Lei Liu, Masakazu Sugiyama, Yu Fu, Chi-Huey Wong.

Abstract

A two-step method has been developed to synthesize several biologically important iminocyclitols in ca. 44-60% yields by using Petasis-type condensation. The method is very general and operationally simple, affording a series of iminocyclitols from easily available sugar derivatives. Unexpected diastereoselectivities are observed, suggesting that the condensation may proceed through a five- or six-membered cyclic iminium ion intermediate.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2009 PMID： 19530721 PMCID： PMC2900252 DOI： 10.1021/ja901656e

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

11 in total

Review 1. Recent developments of transition-state analogue glycosidase inhibitors of non-natural product origin.

Authors: Vinni H Lillelund; Henrik H Jensen; Xifu Liang; Mikael Bols
Journal: Chem Rev Date: 2002-02 Impact factor: 60.622

Review 2. Amino-sugar glycosidase inhibitors: versatile tools for glycobiologists.

Authors: B Winchester; G W Fleet
Journal: Glycobiology Date: 1992-06 Impact factor: 4.313

3. Synthetic iminosugar derivatives as new potential immunosuppressive agents.

Authors: Xin-Shan Ye; Fang Sun; Min Liu; Qin Li; Yuhang Wang; Guisheng Zhang; Li-He Zhang; Xiao-Lian Zhang
Journal: J Med Chem Date: 2005-06-02 Impact factor: 7.446

4. A new route to diverse 1-azasugars from N-Boc-5-hydroxy-3-piperidene as a common building block.

Authors: Hidekazu Ouchi; Yukiko Mihara; Hiroki Takahata
Journal: J Org Chem Date: 2005-06-24 Impact factor: 4.354

5. Carbohydrate Mimetics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition.

Authors:
Journal: Angew Chem Int Ed Engl Date: 1999-08 Impact factor: 15.336

6. Access to piperidine imino-C-glycosides via stereoselective thiazole-based aminohomologation of pyranoses.

Authors: Alessandro Dondoni; Andrea Nuzzi
Journal: J Org Chem Date: 2006-09-29 Impact factor: 4.354

7. alpha- and beta-homogalactonojirimycins (alpha- and beta-homogalactostatins): synthesis and further biological evaluation.

Authors: O R Martin; O M Saavedra; F Xie; L Liu; S Picasso; P Vogel; H Kizu; N Asano
Journal: Bioorg Med Chem Date: 2001-05 Impact factor: 3.641

8. D-Fructose-6-phosphate aldolase-catalyzed one-pot synthesis of iminocyclitols.

Authors: Masakazu Sugiyama; Zhangyong Hong; Pi-Hui Liang; Stephen M Dean; Lisa J Whalen; William A Greenberg; Chi-Huey Wong
Journal: J Am Chem Soc Date: 2007-11-07 Impact factor: 15.419

9. Rhodium-catalyzed decarbonylation of aldoses.

Authors: Rune Nygaard Monrad; Robert Madsen
Journal: J Org Chem Date: 2007-11-03 Impact factor: 4.354

10. Novel five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: new structures for antivirals and osteoarthritis.

Authors: Pi-Hui Liang; Wei-Chieh Cheng; Yi-Ling Lee; Han-Pang Yu; Ying-Ta Wu; Yi-Ling Lin; Chi-Huey Wong
Journal: Chembiochem Date: 2006-01 Impact factor: 3.164

5 in total

Concise synthesis of iminocyclitols via Petasis-type aminocyclization.

Review 1. Recent developments of transition-state analogue glycosidase inhibitors of non-natural product origin.

Review 2. Amino-sugar glycosidase inhibitors: versatile tools for glycobiologists.

3. Synthetic iminosugar derivatives as new potential immunosuppressive agents.

4. A new route to diverse 1-azasugars from N-Boc-5-hydroxy-3-piperidene as a common building block.

5. Carbohydrate Mimetics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition.

6. Access to piperidine imino-C-glycosides via stereoselective thiazole-based aminohomologation of pyranoses.

7. alpha- and beta-homogalactonojirimycins (alpha- and beta-homogalactostatins): synthesis and further biological evaluation.

8. D-Fructose-6-phosphate aldolase-catalyzed one-pot synthesis of iminocyclitols.

9. Rhodium-catalyzed decarbonylation of aldoses.

10. Novel five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: new structures for antivirals and osteoarthritis.

1. Catalytic diastereoselective petasis reactions.

2. An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and catalytic OsO4.

3. Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars.

4. Glycerol as an efficient medium for the petasis borono-mannich reaction.

5. Reactivity and Synthetic Applications of Multicomponent Petasis Reactions.