Positions

Research Areas research areas

Overview

  • I am a Professor in the Department of Chemistry at the University of New Hampshire. I teach and conduct research in the area of organic chemistry, with primary interests in the development of synthetic methodology and the application these new synthetic tools to the preparation of molecules on biological.

    Recent research activity has focused on the development of a series of reactions initiated by the reaction of β-dicarbonyl compounds with zinc carbenoids. Treatment of the resultant reactive intermediate with a variety of electrophiles leads to a diverse array of complex products. The chemistry has been key to the efficient synthesis of numerous natural products, include brefeldin A, papyracillic acids A, B, and C, CJ-12,954 and CJ-13,014, and patulolide A.
  • Publications

    Academic Article

    Year Title
    2014 Discussion Addendum for: Formation of gamma-Keto Esters from beta-Keto Esters: Methyl 5,5-dimethyl-4- oxohexanoateOrganic Syntheses.  91:248-259. 2014
    2012 Syntheses of Papyracillic Acids: Application of the Tandem Chain Extension-Acylation ReactionJournal of Organic Chemistry.  77:9171-9178. 2012
    2012 Small organic solutes in sticky droplets from orb webs of the spider Zygiella atrica (Araneae; Araneidae): β-alaninamide is a novel and abundant component.Chemistry and Biodiversity.  9:2159-2174. 2012
    2012 Tandem chain extension-Mannich reaction: an approach to beta-proline derivativesTetrahedron.  68:7799-7805. 2012
    2012 A combined DFT and NMR investigation of the zinc organometallic intermediate proposed in the syn-selective tandem chain extension-aldol reaction of β-keto esters.Journal of Organic Chemistry.  77:5942-5955. 2012
    2012 Preparation of novel peptide isosteres through a zinc-carbenoid mediated homologation reactionACS National Meeting Book of Abstracts.  243. 2012
    2011 The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1.Bioorganic and Medicinal Chemistry Letters.  21:4597-4601. 2011
    2011 Zinc carbenoid-mediated chain extension: Diastereoselective formation of a cyclopropyl alcohol-containing dipeptide isostereACS National Meeting Book of Abstracts.  241. 2011
    2010 A mechanistic investigation into the zinc carbenoid-mediated homologation reaction by DFT methods: is a classical donor-acceptor cyclopropane intermediate involved?Journal of Organic Chemistry.  75:7322-7331. 2010
    2009 Stereoselective formation of a functionalized dipeptide isostere by zinc carbenoid-mediated chain extension.Journal of Organic Chemistry.  74:645-651. 2009
    2008 Formation of gamma-lactones through CAN-mediated oxidative cleavage of hemiketals.Journal of Organic Chemistry.  73:7409-7412. 2008
    2008 Tandem Chain Extension-Iodomethylation Reactions: Formation of alpha-Functionalized gamma-Keto Carbonyls.Tetrahedron.  64:8045-8051. 2008
    2007 Formation of beta-substituted gamma-keto esters via zinc carbenoid mediated chain extensionSynthesis.  2007:2404-2408. 2007
    2007 Formal synthesis of (+)-brefeldin A: application of a zinc-mediated ring expansion reaction.Journal of Organic Chemistry.  72:4390-4395. 2007
    2006 Stereocontrolled formation of ketomethylene isosteres through tandem chain extension reactions.Journal of Organic Chemistry.  71:8140-8145. 2006
    2003 Zinc carbenoid-mediated chain extension: preparation of alpha,beta-unsaturated-gamma-keto esters and amides.Journal of Organic Chemistry.  68:4535-4538. 2003
    2003 Ring expansions of beta-keto lactones with zinc carbenoids: syntheses of (+)-patulolide A and (+/-)-patulolide B.Journal of Organic Chemistry.  68:1878-1885. 2003
    2003 Chain extension of amino acid skeletons: preparation of ketomethylene isosteresTetrahedron.  59:1521-1527. 2003
    2002 Zinc carbenoid-mediated preparation of unsaturated keto esters and amides.ACS National Meeting Book of Abstracts.  224:U260-U260. 2002
    2002 FORMATION OF b-KETO ESTERS FROM b-KETO ESTERS: METHYL 5,5-DIMETHYL-4-OXOHEXANOATEOrganic Syntheses.  79:146-146. 2002
    2001 Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.Organic Letters.  3:4169-4171. 2001
    2001 Zinc carbenoid-mediated chain extension of beta-keto amidesTetrahedron.  57:8793-8800. 2001
    2001 Tandem chain extension-homoenolate formation: the formation of alpha-methylated-gamma-keto esters.Organic Letters.  3:3037-3040. 2001
    2000 Olefin cross-metathesis in the preparation of polycyclopropanes: formal synthesis of FR-900848Tetrahedron Letters.  41:8723-8727. 2000
    2000 Zinc-mediated chain extension of beta-keto phosphonatesJournal of Organic Chemistry.  65:5615-5622. 2000
    1999 Preparation of 1,4-dioxenes from alpha-diazo-beta-ketoestersHeterocycles.  51:1073-1078. 1999
    1998 Preparation of the zaragozic acid core through the rearrangement of an oxonium ylideTetrahedron Letters.  39:1691-1694. 1998
    1997 Zinc-mediated conversion of beta-keto esters to gamma-keto estersJournal of Organic Chemistry.  62:6444-6446. 1997
    1997 Study of the rearrangements of oxonium ylides generated from ketalsJournal of Organic Chemistry.  62:3902-3909. 1997
    1997 Two-directional synthesis of polycyclopropanes. An approach to the quinquecyclopropane fragment of U-106305Journal of Organic Chemistry.  62:1215-1222. 1997
    1996 Studies on the Diastereoselective Preparation of Bis-cyclopropanes.Journal of Organic Chemistry.  61:8792-8798. 1996
    1996 Ylide-mediated bis-cyclopropane formation: A reversal in substrate-mediated facial selectivityTetrahedron Letters.  37:8341-8344. 1996
    1996 Selectivity in the rearrangements of oxonium ylidesTetrahedron Letters.  37:5053-5056. 1996
    1995 A DIVERGENT DIASTEREOSELECTIVE APPROACH TO BICYCLOPROPANESTetrahedron Letters.  36:5495-5498. 1995
    1995 PREPARATION OF DIALLYL KETALSSynthetic Communications.  25:587-593. 1995
    1994 DIASTEREOSELECTIVE SYNTHESIS OF BICYCLOPROPANESTetrahedron Letters.  35:9181-9184. 1994
    1993 A PHOTOCHEMICALLY TRIGGERED DNA-CLEAVING AGENT - SYNTHESIS, MECHANISTIC AND DNA CLEAVAGE STUDIES ON A NEW ANALOG OF THE ANTITUMOR ANTIBIOTIC DYNEMICINJournal of Organic Chemistry.  58:5867-5869. 1993
    1991 STUDIES ON DNA-CLEAVING AGENTS - SYNTHESIS OF A FUNCTIONAL DYNEMICIN ANALOGJournal of the American Chemical Society.  113:2311-2313. 1991
    1989 NOVEL PALLADIUM (II) MEDIATED REACTIONS OF N-HYDROXY-BETA-LACTAMSTetrahedron Letters.  30:7009-7012. 1989
    1988 TITANIUM(III) MEDIATED SYNTHESIS OF DICARBOXYPYRAZINESHeterocycles.  27:1123-1126. 1988
    1987 Stereoselective synthesis of vinylcyclopropanes via palladium-catalyzed reactionsJournal of Organic Chemistry.  52:5430-5435. 1987
    1987 Purin-6-yl 6-deoxy-1-thio-beta-D-glucopyranoside. Enzymology, chemistry, and cytotoxicity.Carbohydrate Research.  165:299-305. 1987
    1987 Stabilization energies and structures of substituted methyl radicalsJournal of Organic Chemistry.  52:3062-3072. 1987

    Conference Proceeding

    Year Title
    2014 Formal synthesis of CJ-12,954 and CJ-13,014ACS National Meeting Book of Abstracts. 2014
    2014 Formation of spiroketal systems through tandem zinc carbenoid-mediated homologation reactionsACS National Meeting Book of Abstracts. 2014
    2013 Zinc carbenoid-mediated chain extension of amino acid-derived beta-diketonesACS National Meeting Book of Abstracts. 2013
    2012 Synthesis of spirofused cyclic ketalsACS National Meeting Book of Abstracts. 2012
    2012 Tandem chain extension-acylation chemistryACS National Meeting Book of Abstracts. 2012
    2012 Synthetic approaches to papyracillic acids A, B, and CACS National Meeting Book of Abstracts. 2012
    2010 Zinc-mediated chain extension as an approach for the synthesis of papyracillic acid CACS National Meeting Book of Abstracts. 2010
    2009 Controlling the formation of beta-substituted gamma-keto esters via amino acid derived precursorsACS National Meeting Book of Abstracts. 2009
    2009 ORGN 471-Stereoselective tandem chain extension reactionsACS National Meeting Book of Abstracts. 2009
    2008 ORGN 180-Synthesis of beta-proline derivativesACS National Meeting Book of Abstracts. 2008
    2008 CHED 439-Scope of the tandem chain extension-aldol reaction of beta-keto imidesACS National Meeting Book of Abstracts. 2008
    2008 ORGN 255-Zinc carbenoid-mediated chain extension reactions: Application to the synthesis of natural productsACS National Meeting Book of Abstracts. 2008
    2008 ORGN 546-Peptide isostere formation by zinc carbenoid-mediated chain extensionACS National Meeting Book of Abstracts. 2008
    2007 ORGN 1000-Formation of gamma-lactones via CAN-mediated oxidationsACS National Meeting Book of Abstracts. 2007
    2007 ORGN 869-New studies into the stereoselectivty of the zinc-mediated chain extension-aldol reactionACS National Meeting Book of Abstracts. 2007
    2007 ORGN 876-Novel synthetic methodologies toward the synthesis of substituted tetrahydrofuransACS National Meeting Book of Abstracts. 2007
    2006 ORGN 320-Zinc-mediated chain extension: Stereoselective approach to ketomethylene isosteresACS National Meeting Book of Abstracts. 2006
    2005 Conversion of beta-keto carbonyl compounds to a, beta-unsaturated-y-keto carbonyl systems: Application to natural products synthesisACS National Meeting Book of Abstracts. U3151-U3151. 2005
    2005 Studies of the zinc-mediated chain extension reaction: Approaches to beta-amino acids through the use of chiral sulfinimines.ACS National Meeting Book of Abstracts. U414-U415. 2005
    2005 Zinc carbenoid chain extension reactions.ACS National Meeting Book of Abstracts. U537-U537. 2005
    2004 Synthesis of a proposed inhibitor of human cytomegalovirus (HCMV) using a tandem chain extension-aldol reaction approach.ACS National Meeting Book of Abstracts. U133-U133. 2004
    2003 Investigation of the zinc organometallic intermediate in the syn-selective tandem chain extension-aldol reaction of beta-keto esters.ACS National Meeting Book of Abstracts. U134-U134. 2003
    2003 Side chain incorporation in ketomethylene isosteresACS National Meeting Book of Abstracts. U135-U135. 2003
    2002 Preparation of ketomethylene isosteres through zinc carbenoid chemistry.ACS National Meeting Book of Abstracts. U102-U102. 2002
    2002 Tandem chain extension-zinc enolate reactions of aldehyhdes.ACS National Meeting Book of Abstracts. U194-U194. 2002
    2001 Chain extension of amino acid skeletons: Preparation of ketomethylene isosteres.ACS National Meeting Book of Abstracts. U169-U169. 2001
    2001 Zinc-mediated chain extension reactions: Studies in alpha-functionalization.ACS National Meeting Book of Abstracts. U212-U212. 2001
    2000 Tandem chain extension Reformatsky reaction.ACS National Meeting Book of Abstracts. U42-U42. 2000
    2000 Chain extension of alpha-substituted-beta-ketoesters using Furukawa-modified Simmons-Smith conditions.ACS National Meeting Book of Abstracts. U327-U327. 2000
    2000 Zinc-mediated chain extension and Reformatsky reaction of alpha-formyl esters.ACS National Meeting Book of Abstracts. U351-U351. 2000
    1999 Application of chain extension chemistry toward a novel synthetic route to gamma-keto phosphonates.ACS National Meeting Book of Abstracts. U80-U80. 1999
    1999 Chain extensions with zinc carbenoids: Selectivity and mechanistic issues.ACS National Meeting Book of Abstracts. U144-U144. 1999
    1998 Design of a highly versatile strategy for the diastereoselective preparation of polycyclopropanated fatty amides.ACS National Meeting Book of Abstracts. U470-U470. 1998
    1998 Oxonium ylide reactions and the zaragozic acid coreACS National Meeting Book of Abstracts. U554-U554. 1998
    1998 Zinc-mediated homologation of beta-keto phosphonates to gamma-keto phosphonates.ACS National Meeting Book of Abstracts. U554-U554. 1998
    1998 Chain extension reactions with zinc carbenoidsACS National Meeting Book of Abstracts. U107-U107. 1998
    1997 Preparation of 1,4-dioxenes from alpha-diazo-beta-ketoestersACS National Meeting Book of Abstracts. 428-ORGN. 1997
    1997 Zaragozic acid core prepared using oxonium ylidesACS National Meeting Book of Abstracts. 454-ORGN. 1997
    1996 Diastereoselective chemistry of oxonium ylidesACS National Meeting Book of Abstracts. 39-ORGN. 1996
    1996 Two-directional synthesis of polycyclopropanesACS National Meeting Book of Abstracts. 72-ORGN. 1996
    1995 OXINIUM YLIDE FORMATION WITH KETALSACS National Meeting Book of Abstracts. 202-ORGN. 1995
    1995 THE DIASTEREOSELECTIVE SYNTHESIS OF BICYCLOPROPANESACS National Meeting Book of Abstracts. 201-ORGN. 1995
    1995 THE DIASTEREOSELECTIVE SYNTHESIS OF POLYCYCLOPROPANESACS National Meeting Book of Abstracts. 363-ORGN. 1995
    1994 STUDIES ON THE DIASTEREOSELECTIVE SYNTHESIS OF POLYCYCLOPROPANESACS National Meeting Book of Abstracts. 58-ORGN. 1994
    1994 PREPARATION AND REACTIVITY OF DIALLYL KETALSACS National Meeting Book of Abstracts. 264-ORGN. 1994
    1993 PHOTOCHEMICALLY ACTIVATED DYNEMICIN ANALOG - SYNTHESIS, MECHANISTIC AND DNA CLEAVAGE STUDIESACS National Meeting Book of Abstracts. 14-ORGN. 1993

    Patents And Disclosures

    Year Title
    Peptide isosteres based on cyclopropyl alcohol functionality

    Teaching Activities

  • Introduction to CEPS Programs Taught course 2017
  • Stdy/Six Sigma Taught course 2016
  • Introduction to CEPS Programs Taught course 2015
  • Independent Study Taught course 2015
  • Special Topic Taught course 2015
  • Thesis Taught course 2015
  • Doctoral Research Taught course 2014
  • Introduction to CEPS Programs Taught course 2014
  • Thesis Taught course 2014
  • Doctoral Research Taught course 2014
  • Independent Study Taught course 2014
  • Synthetic Organic Chemistry I Taught course 2014
  • Synthetic Organic Chemistry I Taught course 2014
  • Thesis Taught course 2014
  • Education And Training

  • B.A. Chemistry, Messiah College
  • M.S. Medicinal&Pharmaceutical Chem., State University of New York at Buffalo
  • Ph.D. Chemistry, University of Notre Dame
  • Full Name

  • Charles Zercher