Abstract

The basic objective of the proposed research is the development of new reagents and strategies for the synthesis of complex organic molecules and polymers that are of biological interest. New reagents based on metal alkylidene complexes will developed for the synthesis of carbon-carbon double bonds. This chemistry will be designed to take advantage of the full potential of the olefin metathesis reaction in organic synthesis. These studies will involve the development of simple synthesis of tungsten alkylidene complexes to be used in the further studies. In the initial studies these alkylidene reagents will be used to convert esters and amines into vinylethers and enamines. The olefin metathesis reaction will be combined with the carbonylolefination reaction in intramolecular directed cyclizations of organic molecules that contain a carbonyl and an olefin. Olefin metathesis of dienes will result in direct cyclization. The techniques proposed can be used to prepare a family complex organic molecules of biological significance.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM031332-11
Application #
2176092
Study Section
Metallobiochemistry Study Section (BMT)
Project Start
1983-03-01
Project End
1996-03-31
Budget Start
1994-04-01
Budget End
1995-03-31
Support Year
11
Fiscal Year
1994
Total Cost
Indirect Cost

  Institution

Name
California Institute of Technology
Department
Chemistry
Type
Schools of Engineering
DUNS #
078731668
City
Pasadena
State
CA
Country
United States
Zip Code
91125

  Publications

Ogba, O M; Warner, N C; O'Leary, D J et al. (2018) Recent advances in ruthenium-based olefin metathesis. Chem Soc Rev 47:4510-4544
Ahmed, Tonia S; Montgomery, T Patrick; Grubbs, Robert H (2018) Using stereoretention for the synthesis of E-macrocycles with ruthenium-based olefin metathesis catalysts. Chem Sci 9:3580-3583
Ahmed, Tonia S; Grubbs, Robert H (2017) A Highly Efficient Synthesis of Z-Macrocycles Using Stereoretentive, Ruthenium-Based Metathesis Catalysts. Angew Chem Int Ed Engl 56:11213-11216
Martin, David; Marx, Vanessa M; Grubbs, Robert H et al. (2016) A Ruthenium Catalyst for Olefin Metathesis Featuring an Anti-Bredt N-Heterocyclic Carbene Ligand. Adv Synth Catal 358:965-969
Dornan, Peter K; Lee, Daniel; Grubbs, Robert H (2016) Tandem Olefin Metathesis/Oxidative Cyclization: Synthesis of Tetrahydrofuran Diols from Simple Olefins. J Am Chem Soc 138:6372-5
Rosebrugh, L E; Ahmed, T S; Marx, V M et al. (2016) Probing Stereoselectivity in Ring-Opening Metathesis Polymerization Mediated by Cyclometalated Ruthenium-Based Catalysts: A Combined Experimental and Computational Study. J Am Chem Soc 138:1394-405
Li, Jiaming; Grubbs, Robert H; Stoltz, Brian M (2016) Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate. Org Lett 18:5449-5451
Endo, Koji; Grubbs, Robert H (2016) Cationic ruthenium alkylidene catalysts bearing phosphine ligands. Dalton Trans 45:3627-34
Marx, Vanessa M; Sullivan, Alexandra H; Melaimi, Mohand et al. (2015) Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis. Angew Chem Int Ed Engl 54:1919-23
Tang, Grace Y; Pribisko, Melanie A; Henning, Ryan K et al. (2015) An in vitro enzymatic assay to measure transcription inhibition by gallium(III) and H3 5,10,15-tris(pentafluorophenyl)corroles. J Vis Exp :

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