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Literature DB >> 22242696

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

Abstract

The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.

Entities: Chemical

Mesh：

Substances：

Year: 2012 PMID： 22242696 PMCID： PMC3272129 DOI： 10.1021/ol203463n

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

15 in total

1. Synthesis and cytotoxicity of 4'-C- and 5'-C-substituted toyocamycins.

Authors: E Gunic; J L Girardet; Z Pietrzkowski; C Esler; G Wang
Journal: Bioorg Med Chem Date: 2001-01 Impact factor: 3.641

2. Allenyl azide cycloaddition chemistry. 2,3-cyclopentennelated indole synthesis through indolidene intermediates.

Authors: Ken S Feldman; D Keith Hester; Malliga R Iyer; Paul J Munson; Carlos Silva López; Olalla Nieto Faza
Journal: J Org Chem Date: 2009-07-17 Impact factor: 4.354

3. Copper complexes of anionic nitrogen ligands in the amidation and imidation of aryl halides.

Authors: Jesse W Tye; Zhiqiang Weng; Adam M Johns; Christopher D Incarvito; John F Hartwig
Journal: J Am Chem Soc Date: 2008-07-03 Impact factor: 15.419

4. Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates.

Authors: Ken S Feldman; Malliga R Iyer; D Keith Hester
Journal: Org Lett Date: 2006-07-06 Impact factor: 6.005

5. Cyclization Cascade of Allenyl Azides: Synergy Between Theory and Experiment.

Authors: Olalla Nieto Faza; Ken S Feldman; Carlos Silva López
Journal: Curr Org Chem Date: 2010-09-01 Impact factor: 2.180

6. Allenyl azide cycloaddition chemistry. synthesis of pyrrolidine-containing bicycles and tricycles via the possible intermediacy of azatrimethylenemethane species.

Authors: Ken S Feldman; Malliga R Iyer
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

7. Allenyl azide cycloaddition chemistry. photochemical initiation and CuI mediation leads to improved regioselectivity.

Authors: Ken S Feldman; D Keith Hester; Carlos Silva López; Olalla Nieto Faza
Journal: Org Lett Date: 2008-03-18 Impact factor: 6.005

8. Total synthesis of meloscine by a [2+2]-photocycloaddition/ring-expansion route.

Authors: Philipp Selig; Eberhardt Herdtweck; Thorsten Bach
Journal: Chemistry Date: 2009 Impact factor: 5.236

9. Allenyl azide cycloaddition chemistry: exploration of the scope and mechanism of cyclopentennelated dihydropyrrole synthesis through azatrimethylenemethane intermediates.

Authors: Ken S Feldman; Malliga R Iyer; Carlos Silva López; Olalla Nieto Faza
Journal: J Org Chem Date: 2008-06-11 Impact factor: 4.354

10. Cyclization cascade of allenyl azides: a dual mechanism.

Authors: Carlos Silva López; Olalla Nieto Faza; Ken S Feldman; Malliga R Iyer; D Keith Hester Ii
Journal: J Am Chem Soc Date: 2007-05-27 Impact factor: 15.419

7 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