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Literature DB >> 20871902

Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence.

Anass Znabet¹, Job Zonneveld, Elwin Janssen, Frans J J De Kanter, Madeleine Helliwell, Nicholas J Turner, Eelco Ruijter, Romano V A Orru.

Abstract

We have combined the biocatalytic desymmetrization of 3,4-cis-substituted meso-pyrrolidines with an Ugi-type multicomponent reaction followed in situ by a Pictet-Spengler-type cyclization reaction sequence for the rapid asymmetric synthesis of alkaloid-like polycyclic compounds.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20871902 DOI： 10.1039/c0cc02938f

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

13 in total

1. Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade.

Authors: Steven Gunawan; Christopher Hulme
Journal: Tetrahedron Lett Date: 2013-08-14 Impact factor: 2.415

2. Polycyclic compounds by Ugi-Pictet-Spengler sequence.

Authors: Wei Wang; Sarah Ollio; Eberhardt Herdtweck; Alexander Dömling
Journal: J Org Chem Date: 2010-12-29 Impact factor: 4.354

3. Ugi/aldol sequence: expeditious entry to several families of densely substituted nitrogen heterocycles.

Authors: Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal: Angew Chem Int Ed Engl Date: 2012-06-29 Impact factor: 15.336

Review 4. Tetrazoles via Multicomponent Reactions.

Authors: Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal: Chem Rev Date: 2019-02-01 Impact factor: 60.622

5. Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

Authors: Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal: Org Lett Date: 2013-05-29 Impact factor: 6.005

Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence.

1. Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade.

2. Polycyclic compounds by Ugi-Pictet-Spengler sequence.

3. Ugi/aldol sequence: expeditious entry to several families of densely substituted nitrogen heterocycles.

Review 4. Tetrazoles via Multicomponent Reactions.

5. Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

6. Various cyclization scaffolds by a truly Ugi 4-CR.

7. Tricycles by a new Ugi variation and Pictet-Spengler reaction in one pot.

8. Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids.

Review 9. The role of biocatalysis in the asymmetric synthesis of alkaloids.

10. Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions.