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Literature DB >> 23316092

Synthesis studies on the Melodinus alkaloid meloscine.

Abstract

The pentacyclic Melodinus alkaloid (±)-meloscine was synthesized in 19 chemical steps from 2-bromobenzaldehyde through a route featuring an allenyl azide cyclization cascade to deliver the core azabicyclo[3.3.0]octane substructure. Peripheral functionalization of this core included a Tollens-type aldol condensation to set the quaternary center at C(20) and a diastereoselective ring closing metathesis to forge the tetrahydropyridine ring.

Entities: CellLine Chemical Disease Species

Year: 2013 PMID： 23316092 PMCID： PMC3539727 DOI： 10.1016/j.tet.2012.12.032

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

19 in total

1. 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

2. 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

3. 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

4. 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

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. A general strategy for the synthesis of vincamajine-related indole alkaloids: stereocontrolled total synthesis of (+)-dehydrovoachalotine, (-)-vincamajinine, and (-)-11-methoxy-17-epivincamajine as well as the related quebrachidine diol, vincamajine diol, and vincarinol.

Authors: Jianming Yu; Xiangyu Z Wearing; James M Cook
Journal: J Org Chem Date: 2005-05-13 Impact factor: 4.354

Synthesis studies on the Melodinus alkaloid meloscine.

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

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

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

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

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

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

7. A general strategy for the synthesis of vincamajine-related indole alkaloids: stereocontrolled total synthesis of (+)-dehydrovoachalotine, (-)-vincamajinine, and (-)-11-methoxy-17-epivincamajine as well as the related quebrachidine diol, vincamajine diol, and vincarinol.

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

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

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

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

2. Environmentally friendly domino multicomponent strategy for the synthesis of pyrroloquinolinone hybrid heterocycles.

3. Synthesis of a Ribose-Incorporating Medium Ring Scaffold via a Challenging Ring-Closing Metathesis Reaction.