Publications from The University of Toledo
53. Poudel, M; Bustani, Z.; Li, X.;* Zhu, J.* Ring opening of cyclopropylmethylidene with trimethylaluminum: Synthesis of 1-cyclopropylethyl ether as an acid labile protecting group for hydroxyl Protection and carbohydrate synthesis. J. Carbohydr. Chem. 2025, 44, 81-93.
52. Banjara, R.; Thapa, P.; Kela, S. H.; Wu, F.; Zhu, J. Synthesis of 2,3-diazido-2,3-dideoxy-β-D-mannosides and 2,3-diazido-2,3-dideoxy-β-D-mannuronic acid via stereoselective anomeric O-alkylation. Carbohydr. Res. 2024, 545, 109279.
51. Gurung, P. B.; Shine, G.; Zhu, J. Synthesis of Salmonella enteritidis Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl N-1,1-Dimethylpropargyl Carbamate Donors. J. Org. Chem. 2024, 89, 12547–12558.
50. Bhetuwal, B. R.;1 Wu, F.;1 Acharya, P. P.; Thapa, P.; Zhu, J.* “Synthesis of 2-Amino-2-deoxy-β-D-mannosides via Stereoselective Anomeric O-Alkylation of 2N,3O-Oxazolidinone-Protected D-Mannosamine: Synthesis of the Trisaccharide Repeating Unit of Streptococcus pneumoniae 19F Polysaccharide.” Org. Lett. 2023, 25, 4214–4218 (1These authors contributed equally to this work).
49. Hettiarachchi, I. L.; Wu, F.; Stoica, M.; Li, X.;* Zhu, J.* "Potassium carbonate-mediated β-selective anomeric O-alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids." Tetrahedron Lett. 2023, 154511.
48. Gurung, P. B.;1 Thapa, P;1 Hettiarachchi, I. L.; Zhu, J.* “Cationic Gold(I)-Catalyzed Glycosylation with Glycosyl N-1,1-Dimethylpropargyl Carbamate donors.” Org. Biomol. Chem. 2022, 20, 7006 - 7010. https://doi.org/10.1039/D2OB01436J (1 These authors contributed equally to this work.)
47. Thapa, P;1 Gurung, P. B.;1 Hettiarachchi, I. L.; Zhu, J.* “Cationic Gold(I)-Catalyzed Glycosylation with Glycosyl S-3-Butynyl Thiocarbonate Donors.” J. Carbohydr. Chem. 2022, 41, 223-237. https://doi.org/10.1080/07328303.2022.2076863 (1 These authors contributed equally to this work.)
46. Meng, S; Hettiarachchi, I. L.; Bhetuwal, B. R.; Thapa, P; Zhu, J.* “Stereoselective Synthesis of β-D-Manno-heptopyranoside via Cs2CO3-Mediated Anomeric O-Alkylation: Synthesis of Tetrasaccharide Repeat Unit of Bacillus thermoaerophilus Surface-Layer Glycoprotein.” J. Org. Chem. 2022, 87, 6588-6600.
45. Hettiarachchi, I. L.; Meng, S.; Chahine, M.; Li, X; Zhu, J.* “Stereoselective β-Mannosylation via Anomeric O-Alkylation with L-sugar-derived electrophiles.” Eur. J. Org. Chem. 2021, 6682-6687.
44. Meng, S.; Li, X.; Zhu, J.* “Recent Advances in Direct Synthesis of 2-Deoxy Glycosides and Thioglycosides.” Tetrahedron 2021, 88, 132140 (invited submission).
43. Bhetuwal, B. R.; Wu, F.; Meng, S.; Zhu, J.* “Stereoselective Synthesis of 2-Azido-2-deoxy-β-D-mannosides via Cs2CO3-Mediated Anomeric O-Alkylation with Primary Triflates: Synthesis of a Tetrasaccharide Fragment of Micrococcus Luteus Teichuronic Acid.” J. Org. Chem. 2020, 85, 16196-16206.
42. Li, X.; Lowary, T.; Driguez, P.-A.; Pohl, N. L.; Zhu, J. “A New Era of Discovery in Carbohydrate Chemistry.” J. Org. Chem. 2020, 85, 15770-15772.
41. Meng, S.;1 Bhetuwal, B. R.;1 Nguyen, H.;1 Qi, X.; Fang, C.; Saybolt, K.; Li, X.;* Liu, P.;* Zhu, J.* “β-Mannosylation via O-Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans.” Eur. J. Org. Chem. 2020, 2291-2301, DOI: 10.1002/ejoc.202000313. (1 These authors contributed equally to this work.)
40. Meng, S.; Bhetuwal, B. R.; Acharya, P. P.; Zhu, J.* “Facile synthesis of sugar lactols via bromine-mediated oxidation of thioglycosides.” J. Carbohydr. Chem. 2019, 38, 109-126.
39. Acharya, P. P.; Khatri, H. R; Janda, S.; Zhu, J.* “Synthesis and antitumor activities of aquayamycin and analogues of derhodinosylurdamycin A.” Org. Biomol. Chem. 2019, 17, 2691-2704.
38. Zhu, J.; Li, X. “1,2-Bis(dimethylsilyl)benzene.” e-EROS Encyclopedia of Reagents for Organic Synthesis, 2017, DOI: 10.1002/047084289X.rn02082 .
37. Zhu, J.; Li, X. “Pentafluorophenyl trifluoracetate.” e-EROS Encyclopedia of Reagents for Organic Synthesis, 2017, DOI: 10.1002/047084289X.rn02081 .
36. Bhetuwal, B. R.; Woodward, J.; Li, X.;* Zhu, J.* “Stereoselective β-Mannosylation via Anomeric O-Alkylation: Concise Synthesis of β-D-Xyl-(l→2)-β-D-Man-(1→4)-α-D-Glc-OMe, a Trisaccharide Oligomer of the Hyriopsis schlegelii Glycosphingolipid.” J. Carbohydr. Chem. 2017, 36, 162-172.
35. Acharya, P.;1 Baryal, K. N.;1 Reno, C.; Zhu, J.* “Synthesis of S-linked trisaccharide glycal of derhodinosylurdamycin A: Discovery of alkyl thiocyanate as an efficient electrophile for stereoselective sulfenylation of 2-deoxy glycosyl lithium.” Carbohydr. Res. 2017, 448, 103-109. (1 These authors contributed equally to this work.)
34. Li, X.; Zhu, J.* “Glycosylation via Transition-Metal Catalysis: Challenges and Opportunities” Eur. J. Org. Chem. 2016, 4724-4767 (Most accessed in 10/2016).
This work was highlighted in the Journal Front Cover: Eur. J. Org. Chem. 2016, 4719.
33. Li, X.;* Woodward, J.; Hourani, A.; Zhu, D.; Ayoub, S.; Zhu, J.* “Synthesis of the 2-Deoxy Trisaccharide Glycal of Antitumor Antibiotics Landomycins A and E.” Carbohydr. Res. 2016, 430, 54-58.
32. Nguyen, H.; Zhu, D.; Li, X.;* Zhu, J.* “Stereoselective Construction of β-Mannopyranosides via Anomeric O-Alkylation: Synthesis of the Trisaccharide Core of N-linked Glycans.” Angew. Chem., Int. Ed. 2016, 55, 4767-4771. This work was highlighted in TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, Volume: 28, Issue: 164, Pages: E119-E120, https://doi.org/10.4052/tigg.1608.6E
31. Baryal, K. N.; Zhu, J.* “Stereoselective Synthesis of S-linked Hexasaccharide of Landomycin A via Umpolung S-Glycosylation.” Org. Lett. 2015, 17, 4530-4533.
30. Khatri, H. R.; Nguyen, H.; Dunaway, J. K.; Zhu, J.* “Fluoroalcohol-Mediated Reductive Iodonio-Claisen Rearrangement: Synthesis of ortho-substituted allyliodoarene.” Front. Chem. Sci. Eng. 2015, 9, 359-368.
29. Khatri, H. R.; Nguyen, H.; Dunaway, J. K.; Zhu, J.* “Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A.” Chem. Eur. J. 2015, 21, 13553-13557.
28. Li, X.;* Saleh, Z.; Egri, B.; Hourani, A.; Harding, L.; Baryal, K. N.; Zhu, J. “Selective deprotection of benzyl (Bn) ethers in the presence of para-methoxybenzyl (PMB) ethers.” Tetrahedron Lett. 2015, 56, 1420-1422.
27. Zhu, D.; Adhikari, S.; Baryal, K. N.; Abdullah, B. N.; Zhu, J.* “Synthesis of α-Digitoxosides and α-Boivinosides via Chelation-Controlled Anomeric O-Alkylation.” J. Carbohydr. Chem. 2014, 33, 438-451(special issue, invited submission).
26. Zhu, D.; Baryal, K. N.; Adhikari, S.; Zhu, J.* “Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric O-Alkylation with Secondary Electrophiles.” J. Am. Chem. Soc. 2014, 136, 3172-3175.
25. Baryal, K. N.; Zhu, J.* “Stereoselective Synthesis of S-Linked 2-Deoxy Sugars.” Synlett(Synpacts) 2014, 25, 308-312.
24. Baryal, K. N.; Adhikari, S.; Zhu, J.* “Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1’-epi-Digitoxin.” J. Org. Chem. 2013, 78, 12469-12476.
23. Adhikari, S.; Li, X.; Zhu, J.* “Studies of S-But-3-ynyl and gem-Dimethyl S-But-3-ynyl Thioglycoside Donors in Gold-Catalyzed Glycosylations.” J. Carbohydr. Chem. 2013, 32, 336-359 (special issue, invited submission).
22. Nguyen, H.; Khatri, H. R.; Zhu, J.* “Reductive Iodonio-Claisen Rearrangement of Iodothiophene Diacetates with Allylsilanes: Formal Synthesis of Plavix®.” Tetrahedron Lett. 2013, 54, 5464-5466. This work was highlighted in Synfacts, 2013, 9, 1265.
21. Baryal, K. N.; Zhu, D.; Li, X.; Zhu, J.* “Umpolung Reactivity in the Stereoselective Synthesis of S-Linked 2-Deoxyglycosides.” Angew. Chem., Int. Ed. 2013, 52, 8012 –8016. This work was highlighted in Synlett (SYNPACTS) 2014, 25, 308-312.
20. Adhikari, S.; Baryal, K. N.; Zhu, D.; Li, X.; Zhu, J.* “Gold-Catalyzed Synthesis of 2-Deoxy Glycosides Using S-But-3-ynyl Thioglycoside Donors.” ACS Catal. 2013, 3, 57-60.
19. Khatri, H. R.; Zhu, J.* “Synthesis of Complex ortho-Allyliodoarenes by Employing the Reductive Iodonio-Claisen Rearrangement.” Chem. Eur. J. 2012, 18, 12232-12236.
18. Li, X.; Zhu, J.* “Recent Advances in Transition Metal-Catalyzed O-Glycosylations.” J. Carbohydr. Chem. 2012, 31, 284-324 (special issue, invited submission).
Graduate and Postdoc Publications
17. O’Cearbhaill, R. E.; Ragupathi, G.; Zhu, J.; Wan, Q.; Mironov, S.; Yan, G.; Spassova, M. K.; Iasonos, A; Kravetz, S.; Ouerfelli, O.; Spriggs, D. R.; Danishefsky, S. J.; Sabbatini, P. J. “A Phase I Study of Unimolecular Pentavalent (Globo-H-GM2-sTn-TF-Tn) Immunization of Patients with Epithelial Ovarian, Fallopian Tube, or Peritoneal Cancer in First Remission”, Cancers 2016, 8, 46; doi:10.3390/cancers8040046 .
16. Germain, A. R.; Bruggemeyer, D. M.; Zhu, J.; Genet, C.; O’Brien, P.; Porco, J. A., Jr.* “Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-O-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization.” J. Org. Chem. 2011, 76, 2577-2584.
15. Wang, P.; Li, X.; Zhu, J.; Chen, J.; Yuan, Y.; Wu, X.; Danishefsky, S. J.* “Encouraging Progress in the ω-Aspartylation of Complex Oligosaccharides as a General Route to β-N-Linked Glycopolypeptides.” J. Am. Chem. Soc. 2011, 133, 1597-1602.
14. Chen, J.; Wang, P.; Zhu, J.; Wan, Q.; Danishefsky, S. J.* “A Program for Ligation at Threonine Sites: Application to the Controlled Total Synthesis of Glycopeptides.” Tetrahedron 2010, 66, 2277-2283.
13. Zhu, J.; Warren, J. D.; Danishefsky, S. J.* “Synthetic Carbohydrate-Based Anticancer Vaccines: The Memorial Sloan-Kettering Experience.” Expert Rev. Vaccines 2009, 8, 1399-1413.
12. Wang, P.; Zhu, J.; Yuan, Y.; Danishefsky, S. J.* “Total Synthesis of the 2,6-Sialylated Immunoglobulin G Glycopeptide Fragment in Homogeneous Form.“ J. Am. Chem. Soc. 2009, 131, 16669-16671.
11. Zhu, J.; Wan, Q.; Lee, D.; Yang, G.; Spassova, M. K.; Ouerfelli, O; Ragupathi, G.; Damani, P.; Livingston, P. O.; Danishefsky, S. J.* “From Synthesis to Biologics: Preclinical Data on the Chemistry Derived Anticancer Vaccines.” J. Am. Chem. Soc. 2009, 131, 9298-9303. This work was highlighted in Chinese Science Bulletin “Trend” 2008, 53, 2126.
10. Yuan, Y.; Zhu, J.; Li, X.; Wu, X.; Danishefsky, S. J.* “Preparation and Reactions of N-Thioformyl Peptides from Amino Thioacids and Isonitriles.” Tetrahedron Lett. 2009, 50, 2329-2333.
9. Zhu, J.; Wan, Q.; Yang, G.; Ouerfelli, O; Danishefsky, S. J.* “Synthesis of Human Cancer Associated Globo-H (MBr1 Antigen) Glycosylamino acid: Some Mechanistic and Conformational Reinvestigations.” Heterocycles 2009, 79, 441-449.
8. Zhu, J.; Wan, Q.; Ragupathi, G.; George, C. M.; Livingston, P. O.; Danishefsky, S. J.* “Biologics through Chemistry: Total Synthesis of a Proposed Dual Acting Vaccine Targeting Ovarian Cancer by Orchestration of Oligosaccharide and Polypeptide Domains.” J. Am. Chem. Soc. 2009, 131, 4151-4158. This work was highlighted in ACS Chemical Biology “Spotlight”, 2009, 4, 238.
7. Zhu, J.; Wan, Q.; Danishefsky, S. J.* “Synthesis of Biotinylated Tumor Associated Carbohydrate Antigens for Immunological Studies.” Tetrahedron Lett. 2009, 50, 712-714.
6. Zhu, J.; Wu, X.; Danishefsky, S. J.* “On the Preparation of Enantiomerically Pure Isonitriles from Amino Acid Esters and Peptides.” Tetrahedron Lett. 2009, 50, 577-579.
5. Chen, J.; Wan, Q.; Yuan, Y.; Zhu, J.; Danishefsky, S. J.* “Native Chemical Ligation at Valine: A Contribution to Peptide and Glycopeptide Synthesis.” Angew. Chem., Int. Ed., 2008, 47, 8521-8524.
4. Dong, S.; Zhu, J.; Porco, J. A., Jr.* “Enantioselective Synthesis of Bicyclo[2.2.2]octenones Using a Copper-Mediated Oxidative Dearomatization /[4+2] Dimerization Cascade.” J. Am. Chem. Soc. 2008, 130, 2738-2739.
3. Zhu, J.; Porco, J. A., Jr.* “Asymmetric Syntheses of (-)-Mitorubrin and Related Azaphilone Natural Products.” Org. Lett. 2006, 8, 5169-5171.
2. Zhu, J.; Grigoriadis, N. P.; Lee, J. P.; Porco, J. A., Jr.* “Synthesis of the Azaphilones Using Copper-Mediated Enantioselective Oxidative Dearomatization.” J. Am. Chem. Soc. 2005, 127, 9342-9343. This work was highlighted in Synfacts, 2006, 1, 0001.
1. Zhu, J.; Germain, A. R.; Porco, J. A., Jr.* “Synthesis of Azaphilones and Related Molecules by Employing Cycloisomerization of o-Alkynylbenzaldehydes.” Angew. Chem., Int. Ed. 2004, 43, 1239-1243.
* denotes the corresponding author.
Patents
2. Danishefsky, S. J.; Ragupathi, G.; Livingston, P. O.; Zhu, J.; Iyer, K.; Yang, G.; Sabbatini, P. “Multivalent Glycopeptide Constructs and Uses Thereof.” 2011, WO 2011156774.
1. Danishefsky, S.; Zhu, J.; Wan, Q.; Jeon, I.; Kim, W.; Nagorny, P.; Lee, D.; Livingston, P.; Ragupathi, G. “Synthesis of Glycopeptide Constructs for Eliciting Antibodies and for Treating Cancer.” 2010, WO 2010006343.