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

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

Volume: 9 Issue: 15

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

Affiliation:

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

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.

Cite this article as:

Brenneman B. Jehrod and Martin F. Stephen, Ring-Closing Metathesis as a Construct for the Synthesis of Polycyclic Alkaloids, Current Organic Chemistry 2005; 9 (15) . https://dx.doi.org/10.2174/138527205774370478