Ring-Closing Metathesis as a Construct for the Synthesis of Polycyclic Alkaloids

Author(s): Jehrod B. Brenneman, Stephen F. Martin.

Journal Name: Current Organic Chemistry

Volume 9 , Issue 15 , 2005

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Abstract:

Molybdenum and ruthenium alkylidene-catalyzed ring-closing metathesis (RCM) reactions have emerged as key constructs for the facile assembly of the polycyclic frameworks of a variety of natural products. Advances in catalyst development, particularly of highly reactive ruthenium species, have enabled facile ene-ene and ene-yne bond metatheses to create both carbocyclic and heterocyclic systems, sometimes possessing remarkable functional and structural complexity in a single operation. The operational simplicity, ease of handling, and generally high turnover numbers of the ruthenium-catalysts have brought RCM reactions to the forefront of practical carbon-carbon bond forming transformations. Some recent applications of RCM to the synthesis of alkaloid natural products are reviewed.

Keywords: schrock molybdenum catalyst, bridged azabicyclic alkaloids, cross-metathesis, pyrrolidine derivatives, manzamine a, dihydropyridinium species, roseophilin

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Article Details

VOLUME: 9
ISSUE: 15
Year: 2005
Page: [1535 - 1549]
Pages: 15
DOI: 10.2174/138527205774370478
Price: $58