Complex Synthesis

Brochures, Flyers and Other Literature

Success Story: Complex Synthesis: Travoprost (53 KB PDF)

Success Story: Development Increases Yield in Alkaloid Synthesis (31 KB PDF)

A Scalable Process to Pharmaceutically- Useful Cyclobutanones (103 KB PDF)

Dowpharma Scientific Publications
Please find detailed a synopsis of the papers and publications on Complex Synthesis that scientists from Dowpharma^SM have published and contributed to since 1998. Due to copyright law we are unable to reproduce the papers online. As such we have quoted the publication reference.

Development of Efficient Methods to Manufacture Prostaglandin Analogues. 
Fox, M. E.; Jackson, M.; Lennon, I.C.  Chimica Oggi; Chemistry Today,  2007, 25, 58-60.

Criteria for Industrial Readiness of Chiral Catalysis Technology for the Synthesis of Pharmaceuticals. 
McCague, R; Lennon, I. C.  Drug Discovery and Development, Volume 2, Edited by Mukund S. Chorghade.  CRC Press, John Wiley & Sons, Inc., New York, 2007, Chapter 20, p121-139

Use of Achiral (Diphosphine) RuCl2 (Diamine) Precatalysts as a Practical Alternative to Sodium Borohydride for Ketone Reduction. 
de Koning, P. D.; Jackson, M.; Lennon, I. C.  Org. Process Res. Dev., 2006, 10, 1054-1058.

Commercial Synthesis of the Antiglaucoma Prostanoid Travoprost.
Fox, M.; Jackson, M.; Lennon, I. C.; McCague, R. Handbook of Chiral Chemicals, Edited by David Ager. CRC Press, Taylor & Francis, Florida, 2006, Chapter 30, p573-587.

A Convenient and Scaleable Synthesis of 11,12-Diamino-9,10-ethanoanthracene and Its Enantiomers.
Fox, M. E.; Gerlach, A.; Lennon, I. C.; Meek, G.; Praquin, C. Synthesis, 2005, 3196-3198.

A Convergent Synthesis of the 11-Oxa Prostaglandin Analogue AL-12182.
Fox, M. E.; Jackson, M.; Lennon, I. C.; McCague, R J. Org. Chem., 2005, 70, in press.

Zinc-mediated intramolecular acyl and imino transfer reactions of aryl iodides.
Boulton, L. T.; Fox, M. E.; Hodgson, P. B.; Lennon, I. C. Tetrahedron Letters, 2005, 46, 983.

Tandem Formation and [2,3] Rearrangement of Methylene Ammonium Ylides Derived from Amines and the Simmons-Smith Reagent
Aggarwal, V. K.; Fang, G Y.; Charmant, J. P. H.; Meek, G. Org Lett, 2003, 5, 1757.

Highly Diastereoselective Simmons-Smith Cyclopropanation of Allylic Amines
Aggarwal, V. K.; Fang, G. Y.; Meek, G. Org Lett, 2003, 5, 4417

The Synthesis of OSU 6162: Efficient, Large-Scale Implementation of a Suzuki Coupling
Lipton, M. F.; Mauragis, M. A.; Maloney, M. T.; Veley, M. F.; VanderBor, D. W.; Newby, J. J.; Appell, R. B.; Daugs, E. D. Org. Process Res. Dev. 2003, 7, 385.

An Enantioconvergent Synthesis of (R)-4-Aryloxy-1-butyne-3-ols for Prostanoid Side Chains
Fox, M. E.; Jackson, M.; Lennon, I. C.; McCague, R.; Parratt, J. S. Adv. Synth. Catal. 2002, 344, 50.

Synthesis of the potent antiglaucoma agent, Travoprost
Boulton, L. T.; Brick, D.; Fox, M. E.; Jackson, M.; Lennon, I. C.; McCague, R.; Parkin, N.; Rhodes, D.; Ruecroft, G. Org. Process Res. Dev. 2002, 6, 138.

Chemoenzymatic Synthesis of the Four Diastereoisomers of 4-Hydroxypipecolic Acid from N-Acetyl-(R,S)-allylglycine: Chiral Scaffolds for Drug Discovery
Lloyd, R. C.; Smith, M. E. B.; Brick, D.; Taylor, S. J. C.; Chaplin, D. A.; McCague, R. Org. Process Res. Dev. 2002, 6, 762

Asymmetric Addition of Diethylzinc to Aldehydes Catalyzed by β-Amino Alcohols Derived from Limonene Oxide
Steiner, D.; Sethofer, S.G.; Goralski, C. T.; Singaram, B. Tetrahedron: Asymmetry 2002, 13, 1477.

Facile and Efficient Method for the Kinetic Separation of Commercially Available cis- and trans-Limonene Epoxide
Steiner, D.; Ivison, L.; Goralski, C. T.; Appell, R. B.; Gojkovic, J. R.; Singaram, B. A. Tetrahedron: Asymmetry 2002, 13, 2359.

An efficient stereoselective synthesis of Z-(2S)- and Z-(2R)-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid, key intermediates in the synthesis of (2S,4S,5R)-(-)- and (2R,4R,5S)-(+)-bulgecinine
Holt, K. E.; Swift, J. P.; Smith, M. E. B.; Taylor, S. J. C.; McCague, R. Tetrahedron Lett. 2002, 43,1545.

Aminoborohydrides. 12. Novel Tandem Reactions of 2-Halobenzonitriles with Lithium N,N-Dialkylaminoborohydrides
Thomas, S.; Collins, C. J.; Cuzens, J. R.; Spiciarich, D. Goralski, C. T.; Singaram, B. J. Org. Chem. 2001, 66, 1999.

Lithium Aminoborohydrides: Reagents with Multiple Personalities
Goralski, C. T.; Singaram, B.; Collins, C. J.; Cuzens, J. R.; Lanz, M. Chapter 2 in Organoboranes for Syntheses, ACS Symposium Series No. 783, American Chemical Society, Washington, D.C., 2001.

Synthesis of 2,4-Di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indoles, Including Antiasthma Clinical Candidate PNU-142731A
Bundy, G. L.; Banitt, L. S.; Dobrowolski, P. J.; Palmer, J. R.; Schwartz, T. M.; Zimmerman, D. C.; Lipton, M. F.; Mauragis, M. A.; Veley, M. F.; Appell, R. B.; Clouse, R. C.; Daugs, E. D. Org. Process Res. Dev. 2001, 5, 144.

An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffolds for drug discovery
Smith, M. E. B.; Lloyd, M. C.; Derrien, N.; Lloyd, R. C.; Taylor, S. J. C.; Chaplin, D. A.; Casy, G.; McCague, R. Tetrahedron: Asymmetry 2001, 12, 703.

Highly selective directed hydrogenation of single enantiomer 4-(tert-butoxycarbonylamino)-cyclopent-1-enecarboxylic acid methyl esters
Smith, M. E. B.; Derrien, N.; Lloyd, M. C.; Taylor, S. J. C.; Chaplin, D. A.; McCague, R. Tetrahedron Lett. 2001, 42, 1347.

A simple and convenient synthesis of β-amino alcohol chiral auxiliaries based on limonene oxide
Chrisman, W.; Camara, J. S.; Marcellini, K.; Singaram, B.; Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuk, K. K. Tetrahedron Lett. 2001, 42, 5805.

Two Reagents in One
Thomas, S.; Collins, C. J.; Goralski, C. T.; Singaram, B. Chemical Innovation 2000, 30, 31.

New Synthesis of a Protected Ketonucleoside by a Non-Cryogenic Oxidation with TFAA/DMSO
Appell, R. B.; Duguid, R. J. Org. Process Res. Dev. 2000, 4, 172.

Applications of Crystallization Technology in Chiral Synthesis
McCague, R.; Smith A. Innovations in Pharmaceutical Technology, 1999, 99, 100-104, 106.

Yield surface analysis in crystallization of ideal multicomponent stereoisomeric mixtures
Smith, A. A. 14th Int. Symp. Ind. Cryst. (Institution of Chemical Engineers), 1999, 2020.

Aminoborohydrides. 10. The Synthesis of Tertiary Amine-Boranes from Various Benzyl Halides and Lithium N,N-Dialkylaminoborohydrides
Collins, C. J.; Lanz, M.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1999, 64, 2574.

Practical radical cyclizations leading to the construction of near-stereopure quaternary carbon stereogenic centres
McCague, R.; Pritchard, R. G.; Stoodley, R. J.; Williamson, D. S. Chemical Communications, 1998, 2691.

Enantiomeric purity with conglomerates
McCague, R. Manuf. Chem. 1998, 22.

Dynamic diastereomeric salt resolution of narwedine and its transformation to (-)-galanthamine
Chaplin, D. A.; Johnson, N. B.; Paul, J. M.; Potter, G. A. Tetrahedron Lett. 1998, 39, 6777.

The Reduction of Imines and Enamines with Transition Metal Hydrides
Singaram, B. Goralski, C. T. In Transition Metals for Organic Synthesis, Volume 2; Beller, M. And Bolm, C. Eds.; Wiley-VCH, Weinheim, Germany, 1998; pp 147-154.

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