Applications of Olefin Cross Metathesis to Commercial Products

• Published in: Advanced synthesis & catalysis Vol. 344; no. 6-7; pp. 728 - 735
• Main Authors: Pederson, Richard L., Fellows, Ingrid M., Ung, Thay A., Ishihara, Hiroki, Hajela, Sharad P.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.08.2002; WILEY‐VCH Verlag; Wiley
• Subjects: Chemistry; Chemistry, Applied; Chemistry, Organic; cross metathesis; insect pheromones; organocatalysis; pharmaceuticals; Physical Sciences; ruthenium catalyst removal; Science & Technology; ORGANIC CATALYSIS; ROUTE; RUTHENIUM; pharmaceuticals; SEX-PHEROMONE; STRATEGIES; DESYMMETRIZATION; organocatalysis; MOTH; RING-CLOSING METATHESIS; FUNCTIONALIZED OLEFINS; ruthenium catalyst removal; GENERATION; cross metathesis; insect pheromones
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/1615-4169(200208)344:6/7<728::AID-ADSC728>3.0.CO;2-4

In this paper, we will demonstrate the value of olefin cross metathesis as an effective synthetic tool for applications in the agrochemical and pharmaceutical industries. First, we will demonstrate the usefulness of cross metathesis reactions in the efficient synthesis of the major component of the Peach Twig Borer pheromone and the of Omnivorous Leafroller pheromone, insect pheromones are environmentally friendly pest‐controlling agents. Second, we will demonstrate highly efficient cross metathesis routes into novel α,β‐unsaturated carbonyl intermediates. These novel α,β‐unsaturated carbonyl intermediates can be further functionalized into pharmaceutical compounds that are difficult to prepare by the traditional synthetic methodologies. This paper highlights key catalyst‐substrate reactivity variations with different ruthenium olefin metathesis catalysts, highlights cross metathesis reactions and techniques and highlights an efficient ruthenium catalyst removal technique.