Stockdill Group Publications

Independent Publications (*indicates corresponding author, indicates equal authorship, undergraduate co-authors are underlined):

16) Arbour, C. A.; Mendoza, L. G.; Stockdill, J.L.* Recent Advances in the Synthesis of C-Terminally Modified Peptides. Org. Biomol. Chem. 2020, 18, 7253– 7272.

Jenn’s commentary in Chemistry World on the Ishikawa lab’s total synthesis of the unnatural enantiomer of quinine in the article Total synthesis of unnatural enantiomer renews interest in quinine

15) Zhu, S.; Samala, G.; Sletten, E. T.; Stockdill, J. L.,* Nguyen, H. M.* Facile Triflic Acid-Catalyzed -1,2-cis-Thiol Glycosylations: Scope and Application to the Synthesis of S-Linked Oligosaccharides, Glycolipids, Sublancin Glycopeptide and TN/TF Antigens. Chem. Sci. 201910,10475–10480Featured as part of the Chemical Science 2019 HOT Article Collection and on the back cover of the Journal:

     

14) Arbour, C. A.; Belavek, K. J.; Tariq, R.; Mukherjee, S.; Tom, J. K.; Isidro-Llobet, A.; Kopach, M. E.; Stockdill, J. L.* Bringing Macrolactamization Full Circle: Self-Cleaving Head-to-Tail Macrocyclization of Unprotected Peptides via Mild N-Acyl Urea Activation J. Org. Chem. 201984, 1035–1041[Supporting Information]

13) Kondasinghe, T. D.; Saraha, H. Y.; Jackowski, S. T.; Stockdill, J. L.* Raising the Bar On-Bead: Efficient On-Resin Synthesis of alpha-Conotoxin LvIA. Tetrahedron Lett. 201960, 23–28. [Supporting Information]

12) Sirinimal, H. S.; Hebert, S. P.; Samala, G.; Chen, H.; Rosenhauer, G. J.; Schlegel, H. B.;* Stockdill, J. L.* A Synthetic and Computational Study of Tin-Free Reductive Tandem Cyclizations of Neutral Aminyl Radicals. Org. Lett. 201820, 6340–6344. DOI: 10.1021/acs.orglett.8b02456. [Supporting Information – Synthetic, Computational]

11) Arbour, C. A.; Stockdill, J. L.* A mild capping method for SPPS on the N-methyl diaminobenzoyl linker: synthesis of an N-acyl urea appended C. elegans neuropeptide. Tetrahedron Lett. 2018, 59, 3903–3906. [Supporting Information]

10) Lopez, A. M.; Ibrahim, A. I.;‡ Rosenhauer, G. J.; Sirinimal, H. S.; Stockdill, J. L.* Tin-Free Access to the ABC Core of the Calyciphylline A Alkaloids and Unexpected Formation of a D-Ring-Contracted Tetracyclic Core. Org. Lett. 201820, 2216–2219[Supporting Information]

9) Arbour, C. A.; Stamatin, R. E.; Stockdill, J. L.* Sequence Diversification by Divergent C-Terminal Elongation of Peptides. J. Org. Chem. 201883,1797–1803. [Supporting Information]

8) Arbour, C. A.; Kondasinghe, T. D.; Saraha, H. Y.; Vorlicek, T. L.; Stockdill, J. L.* Epimerization-Free Access to C-Terminal Cysteine Peptide Acids, Carboxamides, Secondary Amides, and Esters via Complimentary Strategies. Chem. Sci. 20189, 350–355[Supporting Information]

TOC

7) Arbour, C. A.; Saraha, H. Y.; McMillan, T. F.; Stockdill, J. L. * Exploiting the MeDbz Linker to Generate Protected or Unprotected C-Terminally Modified Peptides. Chem. Eur. J. 2017, 23, 12484–12488[Supporting Information]

TOCgraphic

6) Kondasinghe, T. D.; Saraha, H. Y.; Odeesho, S. B.; Stockdill, J. L.* Direct Palladium-Mediated On-Resin Disulfide Formation from Allocam Protected Peptides. Org. Biomol. Chem. 2017, 15, 2914–2918. [Supporting Information] Selected for inclusion in the themed collection: ‘Celebrating excellence in research: women of organic chemistry.’ RSC Tweet here.

5) Fandrick, D. R.;* Hart, C. A.; Okafor, I. S.; Mercadante, M. A.; Sanyal, S.; Masters, J. T.; Sarvestani, M.; Fandrick, K. R.; Stockdill, J. L.; Grinberg, N.; Gonnella, N.; Lee, H.; Senanayake, C. H. Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines Org. Lett. 2016, 18, 6192–6195. [Supporting Information]

ol-2016-03253g_0010

4) Yang, Y.Y.; Ibrahim, A. A.; Hashemi, P.;* Stockdill, J. L.* Real-Time, Selective Detection of Copper(II) using Ionophore-Grafted Carbon-Fiber Microelectrodes. Anal. Chem. 201688, 6962–6966. [Supporting Information]TOC5 copy

3) Yang, Y.Y; Ibrahim, A. A.; Stockdill, J. L.;* Hashemi, P.* A Density-Controlled Scaffolding Strategy for Covalent Functionalization of Carbon-Fiber Microelectrodes. Anal. Methods 20157, 7352–7357. Part of the 2015 Emerging Investigators Themed Collection [Supporting Information]

TOCcrop

2) Stockdill, J. L.;* Lopez, A. M.; Ibrahim, A. A. Toward the ABCD Core of the Calyciphylline A-Type Daphniphyllum Alkaloids: Solvent non-Innocence in Neutral Aminyl Radical Cyclizations. Tetrahedron Lett. 2015, 56, 3503–3506. Invited Submission to Symposium in Print in Memory of Harry Wasserman. [Supporting Information]

GA

1)  Ibrahim, A. A.; Golonka, A. N.; Lopez, A. M.; Stockdill, J. L.* Rapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-type Daphniphyllum Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical. Org. Lett. 2014, 16, 1072–1075. Highlighted in Doug Taber’s Organic Chemistry Highlights [Supporting Information]

Mentored Publications:

10) Brailsford, J. A.; Stockdill, J. L.; Axelrod, A. J.;* Peterson, M. T.; Vadola, P. A.; Johnston, E. V.; Danishefsky, S. J. Total Chemical Synthesis of Human Thyroid-Stimulating Hormone (hTSH) β-Subunit: Application of Arginine-tagged Acetamidomethyl (AcmR) Protecting Groups. Tetrahedron, 201874, 1951–1956.

9) Bagdanoff, J. T.; Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M.* Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol. Eur. J. Org. Chem. 2016, 2021–2024.

Untitled 00_StockdillLab_documents-18)  Wilson, R. M.; Stockdill, J. L.; Vadola, P. A.; Wu, X.; Li, X.; Park, P. K.; Wang, P.; Danishefsky, S. J. A Fascinating Journey into History: Exploration of the World of Isonitriles as Precursors to Complex Amides. Angew. Chem. Int. Ed. 2012, 51, 2834–2348. 7)  Wu, X.; Stockdill, J. L.; Park, P. K.; Danishefsky, S. J. Expanding the Limits of Isonitrile-Mediated Amidations Through a Second-Generation Synthesis of Cyclosporine: On the Remarkable Stereosubtleties of Macrolactam Formation from Seco-Cyclosporins. J. Am. Chem. Soc. 2012, 134, 2378–2384.

6)  Wu, X.; Stockdill, J. L.; Wang, P.; Danishefsky, S. J. Total Synthesis of Cyclosporine: Access to N-Methylated Peptides via Isonitrile Coupling Reactions. J. Am. Chem. Soc. 2010, 132, 4098–4100.

5)  Stockdill, J. L.; Wu, X.; Danishefsky, S. J. Coupling Reactions of Hindered Alkyl Thioacids and Hindered Isonitriles: Mechanistic Studies. Tetrahedron Lett. 2009, 50, 5152–5155.

4)  Stockdill, J. L.; Behenna, D. C.; McClory, A. M.; Stoltz, B. M. An Efficient Synthesis of the Carbocyclic Core of Zoanthenol. Tetrahedron, 2009, 65, 6571–6575. Invited paper for Tetrahedron Prize Special Issue

3)  Stockdill, J. L.; Behenna, D. C.; Stoltz, B. M.  Unexpected Decarbonylation During an Acid-Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Tetrahedron Lett. 2009, 50, 3182–3184. Invited paper for 50th Anniversary Special Issue

2)  Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M.  The Biology and Chemistry of the Zoanthamine Alkaloids. Angew. Chem. Int. Ed. 2008, 47, 2365–2386.

1)  Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M. Synthesis of the Carbocyclic Core of Zoanthenol: Implementation of an Unusual Acid-Catalyzed Cyclization. Angew. Chem. Int. Ed. 2007, 46, 4077–4079.