***** : Chemical Process R&D, ***** Inc.
Thousand Oaks, CA, USA
Title: Principal Scientist
Drug Substance Team Leader responsible for the development and implementation of novel chemistry for the manufacture of active pharmaceutical ingredients (API). Route selection, optimization, final form selection (salt, polymorph) and multi-kg GMP scale-up of API. Extensive experience in ***** L reactors. Technical writing for patents, regulatory filings, due diligence, tech transfer, development reports and publication of novel research.
CMC Team Leader (integrated team consisting of members from Process R&D, Pharmaceutics R&D, Analytical R&D, Quality and Regulatory Affairs) responsible for strategy and technical issues related to the manufacture and release of drug substance and drug product.
Manage a process research group (4 Ph. D. level, 3 BSc. /MSc level reports). Responsible for career planning and development, mentoring, technical guidance and performance ratings.
***** : Massachusetts Institute of Technology
Cambridge, MA, USA
Post-Doctoral Research. Advisor: Stephen L. Buchwald.
A new generation of biphenyl based phosphine ligands (e. g. SPhos) were developed for use in Pd-catalyzed cross-coupling reactions. Structural refinements to the ligand backbone provided catalysts with superb reactivity in Suzuki Miyaura cross-couplings. General and efficient syntheses of sterically hindered biaryls, heteroaryls and mild couplings of alkylboron derivatives were achieved at low catalyst loadings. Remarkably high turnover numbers (TON) were obtained for the reactions of unactivated aryl halides.
***** : University of British Columbia
Vancouver, BC, Canada
Doctoral Research. Advisor: Edward Piers.
A general synthetic strategy for the variecolin class of sesterterpenoids was developed. A sequential annulation approach was employed to establish each of the carbocyclic rings present in these structurally related substances. Highlights of the approach include the use of bifunctional reagents for expedient ring formation as well as the exploitation of conformational effects and molecular topography for stereoselective bond construction. A new cycloheptenone annulation method was developed and a key remote functionalization strategy was applied to the first total syntheses of variecolin, variecolol and variecolactone.
1995: Merck Frosst Inc. Pointe Claire-Dorval, QC, Canada
Medicinal Chemistry Research. Advisor: Yongxin Han.
Working in the department of Medicinal Chemistry, research focused on the development of a 'traceless' silicon based linking technology for solid phase synthesis. A method was devised for attaching haloarylsilanes to a polymer support that could then be cleaved by a variety of electrophiles (e. g. H+, ICl, Br2) to give the desired ipso-substitution products. Suzuki cross-coupling reactions on the polymer bound haloarylsilanes were also performed. High yields of biaryls were obtained upon electrophilic cleavage of the coupled resins and an exploration of other aromatic scaffolds for rapid analogue synthesis was conducted.
***** : McGill University
Montreal, QC, Canada
Undergraduate Thesis Research. Advisor: Romas J. Kazlauskas.
The Candida rugosa lipase catalyzed hydrolysis, transesterification and amidation reactions of chiral esters were investigated.
1994: Pulp and Paper Research Institute of Canada
Pointe Claire, QC, Canada
Undergraduate Research. A study of the reactivity of beta-1 lignols with alkali and oxygen was conducted to determine their susceptibility to oxidative degradation and the underlying chemical mechanisms.
1993: McGill University Pulp and Paper Center
Montreal, QC, Canada
Undergraduate Research. NMR investigation of products produced from lignin photo irradiation.
'Selective Catalytic Hydrogenation of Nitro Groups in the Presence of Activated Heteroaryl Halides' Annie J. Kasparian, Cecile Savarin, Allan M. Allgeier, Shawn D. ***** ***** . Chem. 2011, ASAP article (DOI: 10. 1021/jo ***** )
'Catalytic Asymmetric Synthesis of a Tertiary Benzylic Carbon Center via Phenol-Directed Alkene Hydrogenation' Seb Caille, Richard Crockett, Krishnakumar Ranganathan, Xiang Wang, Jacqueline C. S. Woo, Shawn D. ***** ***** . Chem. 2011, 76, 5198 (Featured Article).
'Development of a Scalable Synthesis of a GPR40 Receptor Agonist' Shawn D. ***** , Christopher J. Borths, Evan DiVirgilio, Liang Huang, Pingli Liu, Henry Morrison, Kiyoshi Sugi, Masahide Tanaka, Jacqueline C. S. Woo, Margaret M. Faul Org. Process. Res. Dev. 2011, 15, 570
'Development of a Suitable Salt Form of a GPR40 Agonist' Henry Morrison, Jonan Jona, Shawn D. ***** , Jacqueline C. S. Woo, Lan Li, Jan Fang Org. Process. Res. Dev. 2011, 15, 104
'Rational Screening Approach for Classical Chiral Resolution under Thermodynamic Equilibrium: A Case Study of Diphenyl-Substituted N-Methyl-Piperazine' Helming Tan, Sheng Cui, Kyung Gahm, Van Luu, Shawn D. ***** Org. Process. Res. Dev. 2011, 15, 53.
'Highly Enantioselective Hydrogenation of Styrenes Directed by 2'-Hydroxyl Groups' Xiang Wang, Anil Guram, Seb Caille, Jack Hu, J. Preston, Michael Ronk, Shawn D. ***** , Org. Lett. 2011, 13, 1881.
'Asymmetric Syntheses of a GPR40 Receptor Agonist via Diastereoselective and Enantioselective Conjugate Alkynylation' Jacqueline C. S. Woo, Sheng Cui, Shawn D. ***** , Margaret M. Faul Tetrahedron 2010, 66, 4730. (Tetrahedron-Symposium-In-Print for Prof. Brian Stoltz's Young Investigator Award).
'Practical Asymmetric Conjugate Alkynylation of Meldrum’s Acid Derived Acceptors: Access to Chiral β-Alkynyl Acids' Sheng Cui, Shawn D. ***** , Jacqueline C. S. Woo, Christopher Borths, Hershel Mukherjee, Maosheng J. Chen, Margaret M. Faul J. Am. Chem. Soc. 2010, 132, 436.
'Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions of 4-Oxobutenamides' Jamie Zigterman, Jacqueline C. S. Woo, Shawn D. ***** , Jason Tedrow, Christopher Borths, Emilio Bunel, Margaret M. Faul ***** . Chem. 2007, 72, 8870.
'Preparation and Decarboxylative Rearrangement of (Z)-Enyne Esters' Jacqueline C. S. Woo, Shawn D. ***** , Margaret M. Faul Tetrahedron Letters, 2007, 48, 5679.
'Catalysts for Suzuki-Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure. ' Timothy E. Barder, Shawn D. ***** , Joseph R. Martinelli, Stephen L. Buchwald J. Am. Chem. Soc. 2005, 127, 4685. (Most-cited JACS article in 2005)
'A Rationally Designed Universal Catalyst for Suzuki-Miyaura Coupling Processes. ' Shawn D. ***** , Timothy E. Barder, Joseph R. Martinelli, Stephen L. Buchwald Angew. Chem. Int. Ed. 2004, 43, 1871. (Most-cited ACIEE communication in ***** )
'A New Cycloheptenone Annulation Method: Use of the Bifunctional reagent (Z)-5-Iodo-1-tributylstannylpent-1-ene in Organic Synthesis' Edward Piers, Shawn D. ***** , Ralph Armbrust J. Chem. Soc. Perkin Trans. 1, 2000, 635.
'Sequential Anionic 1, Ester Shifts and Intramolecular Stille Couplings: A New Protocol for the Concise Assembly of Functionalized Polycyclic Dienes' Edward Piers, Miguel Romero, Shawn D. ***** Synlett, 1999, 1082.
'Silicon Directed ipso-Substitution of Polymer Bound Arylsilanes: Preparation of Biaryls via the Suzuki Cross-Coupling Reaction' Yongxin Han, Shawn D. ***** , Robert N. Young Tetrahedron Letters, 1996, 37, 2703.
***** : Chemical Process R&D, ***** Inc.