Ring-closing Metathesis Approach Research Articles

Gram Scale-up Synthesis of all-(Z)-Cyclododecatetraene: A Comparison between Intramolecular Wittig and Ring Closing Metathesis Approaches

A total synthesis of all-(Z)-cyclododeca-1,4,7,10-tetraene was achieved in 28% overall yield using an intramolecular Wittig reaction as key step while an approach based on ring closing metathesis was found ineffective.

Carbohydrate based formal synthesis of stemoamide using ring-closing metathesis

A synthesis of stemoamide has been achieved from d-glucose. The stereocontrolled allylation under Barbier reaction conditions led to the installation of the 2-pyrrolidinone ring at C-3 followed by a ring-closing metathesis approach to construct the azepine ring system.

Metathesis in the presence of a transition metal alkyne complex

A ring closing metathesis approach to medium sized rings is described. The methodology succeeds in the presence of a transition metal alkyne complex.

Copper(I)- or Iron(II)-Templated Synthesis of Molecular Knots Containing Two Tetrahedral or Octahedral Coordination Sites

Molecular trefoil knots have been prepared from metal-assembled precursors using the ring closing metathesis (RCM) cyclization methodology. The templating metal is either copper(I) or iron(II) and the coordinating fragments 1,10-phenanthroline or 2,2‘:6‘,2"-terpyridine, respectively. The RCM approach, newly applied to the field of catenanes and knots, represents a spectacular synthetic improvement in terms of yield and experimental conditions (no high dilution required). The dicopper(I) trefoil knot has been synthesized in a 74% yield. A similar approach also led to the first knot constructed around two iron(II) bis(terpyridine) moieties, demonstrating that iron(II) can also be used as a highly efficient template. Moreover, for both Cu(I) and Fe(II) knots, it has been possible to quantitatively reduce the cyclic olefins formed during the macrocyclization by catalytic (Pd/C) hydrogenation. An X-ray structure of the double helix of iron(II) bis(1,2-bis(5-(5"-methyl-2,2‘:6‘,2"-terpyridinyl))ethane) is given which shows that the double-stranded helical precursor is well predisposed for the formation of a molecular knot.