Fearnley, Stephen
 

Fearnley, Stephen


Associate Professor
Chemistry

Phone: 718-262-2660
Office Location: AC-3F01D
sfearnley@york.cuny.edu

Education

Degree Institution Field Dates
PhD  University of Salford  Organic Chemistry  1992 
BS  Sheffield City Polytechnic  Applied Chemistry  1988 

As a synthetic organic chemist, my research involves development of new methodology for the construction of bioactive natural products: alkaloids, cyclic ether arrays, & C-glycosides. Current studies include:

• Investigation & use of oxazolone as a useful heterocyclic scaffold for alkaloid synthesis - studies of intramolecular Diels-Alder reactions with oxazolone as dienophile.

• Novel organosilane chemistry for approaches to bioactive ethers - concise assembly of cis-fused bicyclic ether arrays via intramolecular attack of vinylsilanes at tethered oxocarbenium ions. A related silyl-activated Friedel-Krafts process requires an unusual combination of electronic & steric effects.

Recently completed targets include 2-epi-pumiliotoxin C & deoxyaltholactone. Similar approaches to gephyrotoxin & dysiherbaine are underway.

Areas of Expertise

Organic Synthesis
Organic Reactions
Natural Products

Articles in Field Of Expertise

As independent Researcher:. "." . : .

S. P. Fearnley* & P. M. Lory. "Vinylsilane-Mediated Synthesis of Styryllactone Analogs." Tetrahedron. 72 2016: 1161-1167.

S. P. Fearnley* & P. M. Lory. "A concise synthesis of (±)-3-deoxyisoaltholactone." Tetrahedron Letters. 55 2014: 5207-5209.

S. P. Fearnley* & C. Thongsornkleeb. "Oxazolone Cycloadducts as Heterocyclic Scaffolds for Alkaloid Construction: Synthesis of (±)-2-epi-Pumiliotoxin C." Journal of Organic Chemistry. 75 2010: 933-936.

S. P. Fearnley* & P. M. Lory. "Intramolecular Vinylsilane–Oxocarbenium Condensations – Concise Assembly of cis-Bicyclic Ether Arrays." Organic Letters. 9 2007: 3507-3510.

S. P. Fearnley*. "2-(3H)-oxazolone – A Simple Heterocycle with Manifold Potential." Current Organic Chemistry; Volume 8, Asymmetric Synthesis. 8 2005: 1289-1338.

S. P. Fearnley* & M. W. Tidwell. "Cyclization of Aryl Silanes with Unexpected Retention of Silicon." Organic Letters. 4 2002: 3797-3798.

S. P. Fearnley* & E. Market. "Intramolecular Diels-Alder Reactions of N-Substituted Oxazolones." Chemical Communications. 2002: 438-439.

...plus 15 others as co-author. "." . : .

Reviews in Field Of Expertise

"Applied Organometallic Chemistry" 10 November 2011: 892-893.

 

Presented Papers, Lectures, and Exhibitions and Performances

" Heterocyclic Motifs for Natural Products Synthesis " 6/5/17: 45th Mid-Atlantic Regional Meeting of the ACS, Hershey PA.

" Synthetic Studies Toward Gephyrotoxin 287C " 6/5/17: 45th Mid-Atlantic Regional Meeting of the ACS, Hershey PA.

" Computational Studies of Intramolecular Diels–Alder Reactions: N-Substituted Oxazolone Trienes " 6/5/17: 45th Mid-Atlantic Regional Meeting of the ACS, Hershey PA.

" Oxazolone Cycloadducts as Versatile Frameworks for Alkaloid Synthesis " 6/11/16: 44th Mid-Atlantic Regional Meeting of the ACS, Riverdale NY.

" Heterocyclic Motifs for Natural Products Synthesis " 6/11/16: 44th Mid-Atlantic Regional Meeting of the ACS, Riverdale NY.

" Oxazolone Cycloadducts as Versatile Frameworks for Alkaloid Synthesis " 3/13/16: 251st ACS National Meeting, San Diego, CA.

" Heterocyclic Methodology for Natural Products Synthesis " 3/3/16: Long Island Sub-Section of the ACS, Queensborough Community College.

" Oxazolone – a Latent 1,2-Aminoalcohol Motif for Alkaloid Synthesis " 10/2/15: The Robert Bittmann Memorial Symposium, CUNY–Queens College.

" Oxazolone Cycloadducts as Versatile Frameworks for Alkaloid Synthesis " 6/12/15: 2015 Northeast Regional Meeting of the ACS, Ithaca, NY.

" Heterocyclic Motifs for Natural Products Synthesis " 6/10/15: 2015 Northeast Regional Meeting of the ACS, Ithaca, NY.

" Heterocyclic Motifs for Natural Products Synthesis " 10/25/13: 2013 Northeast Regional Meeting of the ACS, New Haven, CT.

" Synthetic Approaches toward Gephyrotoxin " 10/24/13: 2013 Northeast Regional Meeting of the ACS, New Haven, CT.

" Heterocyclic Methodology for Natural Products Synthesis " 9/26/13: CUNY–College of Staten Island.

" Heterocyclic Motifs for Natural Products Synthesis " 6/23/13 to 6/27/13: 43rd National Organic Chemistry Symposium, University of Washington, WA.

" From Queens to ... Queen & Country? A year’s sabbatical in Cambridge " 5/2/13: CUNY–York College.

" Studies toward the Total Synthesis of Madeirolide A " 4/7/13: 245th ACS National Meeting, New Orleans, LA.

" From Queens to ... Queen & Country? A year’s sabbatical in Cambridge " 4/5/13: CUNY–Brooklyn College.

" Heterocyclic Motifs for Natural Products Synthesis " 10/17/11: University of Cambridge.

" Heterocyclic Motifs for Natural Products Synthesis " 11/29/10: CUNY–Queens College.

" Heterocyclic Methodologies for Natural Products Synthesis " 8/13/10 to 8/16/10: 14th Symposium on the Latest Trends in Organic Synthesis, St. Catherines, ON, Canada.

" New Heterocyclic Methodology for the Synthesis of Bioactive Natural Products " 7/20/10: York College 2010 Summer Bridge to Research, Jamaica NY.

" Heterocyclic Motifs for Natural Product Architecture " 11/9/09: CUNY–City College.

" Oxazolone Cycloadducts as Versatile Scaffolds for Alkaloid Synthesis " 8/13/08 to 8/16/08: 13th Symposium on the Latest Trends in Organic Synthesis, St. Catherines, ON, Canada.

" Novel Organosilane Chemistry for Approaches to Bioactive Ether Targets " 8/13/08 to 8/16/08: 13th Symposium on the Latest Trends in Organic Synthesis, St. Catherines, ON, Canada.

" Oxazolone Cycloadducts as Versatile Scaffolds for Alkaloid Synthesis " 5/21/08: 40th Mid-Atlantic Regional Meeting of the ACS, Queensborough College NY.

" Novel Organosilane Chemistry for Approaches to Bioactive Ether Targets " 5/18/08: 40th Mid-Atlantic Regional Meeting of the ACS, Queensborough College NY.

" Intramolecular Diels-Alder Reactions of Oxazolone: Approaches toward Total Synthesis of Pumiliotoxin C and Related Alkaloids " 8/21/07: 234th ACS National Meeting, Boston MA.

" Cis-Fused Bicyclic Ether Arrays as a General Framework for Natural Product Synthesis " 8/21/07: 234th ACS National Meeting, Boston MA.

" New Rings for Old – Heterocyclic Methodology for the Construction of Natural Product Architecture " 1/12/07: CUNY–The Graduate Center.

" Intramolecular vinylsilane-oxonium cyclizations - A rapid assembly of cis-fused ether arrays " 7/16/06 to 7/21/06: Gordon Research Conference “Organic Reactions & Processes” – Bryant College, RI.

" New Methodology for the Construction of Polycyclic Ether Arrays (and more besides…) " 9/9/05: CUNY–Brooklyn College.

" Cis-Fused Polycyclic Ether Arrays: A Generalized Approach " 9/11/03: 226th ACS National Meeting, New York NY.

" ...plus an additional 17 Invited Lectures, 13 Presentations and 42 presentations by student co-workers " : .

Professional Honors, Prizes, Fellowships

Visiting Scholar, St. Edmund’s College, University of Cambridge: 2011-12.

City University of New York Fellowship Leave Recipient: 2011-12.

Lamar University Merit Award: 2003.

Gill Science Faculty Development Award, The Gill Foundation: 2000.

Royal Society of Chemistry—Society of Chemists in Industry Greater Manchester Prize Colloquium Competition: 1991.

Ultrafine Chemicals Trophy: 1991.

Grants-In-Aid

NIH MBRS-SCORE SC3, Oxazolone Cycloadducts as Heterocyclic Scaffolds for Decahydroquinoline Alkaloid Synthesis. 4/13 to present: $498,250.

NIH MBRS-SCORE SC3, Oxazolone Cycloadducts as Heterocyclic Scaffolds for Alkaloid Synthesis: Gephyrotoxin 287C. 4/11 to 3/15 [relinquished 11/11]: $490,647.

NIH MBRS-SCORE, Bioactive Alkaloid Synthesis via Oxazolone Cycloaddition. 2/06 to 6/10: $474,479.

ACS-PRF, Intramolecular Cycloadditions of N-Substituted Oxazolone. 9/02 to 8/06: $35,000.

The Welch Foundation, A New & Versatile Approach to Structurally Diverse Bioactive Ethers. 6/00 to 5/03: $145,000.

PSC-CUNY, Rounds 35, 36, 38, 40, 41, 43, 44 & 48. 04 to present: $31,328 total.

Offices Held In Professional Societies

Member of the American Chemical Society, Organic Division: 1994 to present.

Other Professional Activities and Public Service

Proposal Reviews for Granting Agencies: National Science Foundation, American Chemical Society Petroleum Research Fund, Professional Staff Congress–City University of New York.

Manuscript Reviews for Publications: Organic Letters, Tetrahedron Letters, Bioorganic & Medicinal Chemistry Letters, Synlett, Research Letters in Organic Chemistry, Marine Drugs, ACS Combinatorial Science.