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Literature DB >> 21381682

Total synthesis of (±)-meloscine.

Yujiro Hayashi¹, Fuyuhiko Inagaki, Chisato Mukai.

Abstract

The total synthesis of (±)-meloscine was completed in a highly stereoselective manner starting from the known 4-(2-aminophenyl)-2,3-dihydro-N-methoxycarbonylpyrrole. The crucial step in this total synthesis involves the efficient construction of the tetracyclic framework of the target natural product by the intramolecular Pauson-Khand reaction.

Entities: Chemical

Mesh：

Substances：

Year: 2011 PMID： 21381682 DOI： 10.1021/ol200311y

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

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Cited

12 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines.

Authors: Hanmo Zhang; E Ben Hay; Steven J Geib; Dennis P Curran
Journal: J Am Chem Soc Date: 2013-11-06 Impact factor: 15.419

3. Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

Authors: Ken S Feldman; Joshua F Antoline
Journal: Org Lett Date: 2012-01-13 Impact factor: 6.005

4. A short total synthesis of (±)-epimeloscine and (±)-meloscine enabled by a cascade radical annulation of a divinylcyclopropane.

Authors: Hanmo Zhang; Dennis P Curran
Journal: J Am Chem Soc Date: 2011-06-16 Impact factor: 15.419

10. Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy.

Authors: Iain Coldham; Adam J M Burrell; Hélène D S Guerrand; Luke Watson; Nathaniel G Martin; Niall Oram
Journal: Beilstein J Org Chem Date: 2012-01-18 Impact factor: 2.883

Total synthesis of (±)-meloscine.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines.

3. Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

4. A short total synthesis of (±)-epimeloscine and (±)-meloscine enabled by a cascade radical annulation of a divinylcyclopropane.

5. Highly functionalized donor-acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids.

6. Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs.

7. A palladium-catalyzed vinylcyclopropane (3+2) cycloaddition approach to the Melodinus alkaloids.

8. Divergent Total Syntheses of (-)-Pseudocopsinine and (-)-Minovincinine.

9. Synthesis studies on the Melodinus alkaloid meloscine.

10. Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy.