JASON JOSEPH CHRUMA

Jason Chruma was born and raised in the Phoenix Metropolitan Area of Arizona (USA) and earned his BS in Chemistry with Honors from the University of Arizona in 1997 working under the mentorship of Prof. Robin Polt. In 2002, he earned his PhD from the University of Pennsylvania studying under Prof. Amos B. Smith, III, and this was followed by an NIH post-doctoral fellowship at Columbia University from 2003-2005 with Prof. Ronald C. Breslow. He began his independent career as an Assistant Professor in the Department of Chemistry at the University of Virginia in 2005 before moving in August of 2012 to Sichuan University where he is now a Professor and Director of Doctoral Studies.  

Honors and Awards

Director of Outstanding Undergraduate Thesis Award – 2nd Rank (2014)

Sichuan University Top-Notch Undergraduate Teacher Award (2013)

National Institutes of Health (USA) Postdoctoral Fellowship (2003-2005)

Wyeth-Ayerst American Chemistry Society Organic Chemistry Division Pre-Doctoral Fellowship (2000-2001)

Admission Direction to Ph.D. Program and Postdoctoral Associates

1.Organic Chemistry: Organic Synthesis; Transition-Metal Catalysis; Natural Product Total Synthesis

2.Bioorganic Chemistry: Small-Molecule Peptidomimemics, g-Amino Acid-based Foldamers; Modulation of Cellular Differentiation

3.Green Chemistry: Green Organic Synthesis

4.Physical Organic Chemistry: Synthesis and Evaluation of Single-Crystal Organic Spintronic Devices (in collaboration with the College of Physical Sciences and Technology)

Research Interests

Prof. Chruma’s research interest focus on developing new methods for the synthesis of nitrogen-containing organic compounds and other biologically-active natural products involving such “green” methods as transition-metal catalyzed decarboxylative alkylations and intramolecular pericyclic reactions. The intent is to discover new molecular probes and tools to elucidate the biomolecular mechanisms involved in cellular differentiation and aniokis. Additional interests involve the design and synthesis of novel foldamer scaffolds and fluorescent linchpin reagents for bioconjugate synthesis.

List of Publications (as of 14 September 2017)

1. J. Yao, W. Wu, W. Liang, D. Zhou, J. J. Chruma, G. Fukuhara, T. Mori, Y. Inoue, C. Yang* “Temperature-Driven Planar Chirality Switching of a Pillar[5]arene-based Molecular Universal Joint” Angew. Chem. Int. Ed. 2017, 56(24), 6869-6873. [DOI: 10.1002/anie.201702542] [SCI B, IF:11.994]

2. Z. Yan, Q. Huang, W. Liang, X. Yu, D. Zhou, W. Wu, J. J. Chruma, C. Yang* “Enantiodifferentiation in the Photoisomerization of (Z,Z)-1,3-Cyclooctadiene in the Cavity of g-Cyclodextrin─Curcubit[6]uril-Wheeled [4]Rotaxanes with an Encapsulated Photosensitizer” Org. Lett. 2017, 19(4), 898-901. [DOI:10.1021/acs.orglett.7b00057] [SCI C, IF: 6.579]

3. C. Fan, W. Wu, J. J. Chruma, J. Zhao, C. Yang* “Enhanced Triplet-Triplet Energy Transfer and Upconversion Fluorescence through Host-Guest Complexation” J. Am. Chem. Soc. 2016, 138(47), 15405-15412. [DOI:10.1021/jacs.6b07946] [SCI B, IF: 13.858]

4. M. Xiang, Y. Wu, J. P. Burke, J. J. Chruma* “High p-Facial and exo-Selectivity for the Intramolecular Diels-Alder Cycloaddition of Dodeca-3,9,11-trien-5-one Precursors to 2-epi-Symbioimine and Related Compounds” J. Org. Chem. 2016, 81(18), 8508?8519. [DOI:10.1021/acs.joc.6b01677]. [SCI C, IF: 4.849]

5. S. Tang, J. Y. Park, A. A. Yeagley, M. Sabat, J. J. Chruma* ―Decarboxylative Generation of 2-Azaallyl Anions: 2-Iminoalcohols via a Decarboxylative Erlenmeyer ReactionOrg. Lett.,201517, 2042–2045 [DOI:10.1021/acs.orglett.5b00107]. SCI C

6. X. Qian, P. Ji, C. He, J.-O. Zirimwabagabo, M. M. Archibald, A. A. Yeagley, J. J. Chruma*,”Palladium-Catalyzed Decarboxylative Generation and Asymmetric Allylation of α-Imino Anions” Org. Lett.2014, 16, 52285231. [DOI:10.1021/ol502693r]. SCI C [Highlighted by M. Lautens & S. Kress in Synfacts 2014, 10(12), 1293. DOI: 10.1055/s- 0034-1379463]

7. Xiang,H.-f.; *Cheng,J.-h.; Ma,X.-f.; Zhou, X.-g.;Chruma, J. J. “Near-Infrared Phosphorescence: Materials and Applications” ChemSoc.Rev.2013, 42, 6128-6185. [DOI:10.1039/C3CS60029G]

8. Li, Z.; Jiang, Y.-Y.; Yeagley, A. A.;Bour, J. P.; Liu, L.;Chruma,J. J.;* Fu, Y.*“Mechanism  of the Pd-catalyzed Decarboxylative Allylation of a-Imino Esters: Decarboxylation via Free Carboxylate Ion” Chem. Eur. J.201218(45), 14527–14538. [DOI: 10.1002/chem.201201425]

9. Burke, J. P.; Sabat, M.; Myers, W. H.;Chruma, J. J.* “Unexpected exo Selectivity for an Intramolecular Diels-Alder Reaction Involving a Doubly-Activated d-Pentenolide Dienophile” Tetrahedron:Asymmetry201122, 31-35. [DOI: 10.1016/j.tetasy.2010.12.018]

10. Burke, J. P.; Sabat, M.;Iovan, D. A.; Myers, W. H.;Chruma, J. J.* “Exploring the Original Proposed Biosynthesis of (+)-Symbioimine: Remote Exocyclic Stereocontrol in a Type I IMDA Reaction,” Org. Lett.201012, 3192-3195. [DOI: 10.1021/ol101141a]  [Highlighted by ChemViewson WILEY-VCH and ChemPubSoc Europe’s online literature review, 18 June 2010:http://www.chemistryviews.org/details/news/743307/Old_Haunts_Revisited.html]

11.Bullock, G. C.; Delehanty, L. L.; Talbot, A. L.; Gonias, S. L.; Tong, W.-H.;Rouault, T. A.; Dewar, B.; Macdonald, J. M.;Chruma,J. J.; Goldfarb, A. N.* "Iron Control of Erythroid Development by a Novel Aconitase-Associated Regulatory Pathway," Blood2010116, 97-108. [DOI:10.1182/blood-2009-10-251496]

12. Fields, W. H.;Chruma, J. J.* "Palladium-Catalyzed Decarboxylative Benzylation of Diphenylglycinate Imines," Org. Lett.201012(2), 316–319. [DOI: 10.1021/ol902651j[Highlighted byP. Knochel and T. Thaler in Synfacts20104, 461. DOI: 10.1055/s-0029-121960]

13. Yeagley, A. A.;Lowder, M. A.;Chruma, J. J.* "Tandem C–C Bond-Forming Processes: Interception of the Pd-Catalyzed Decarboxylative Allylation of Allyldiphenylglycinate Imines with Activated Olefins." Org. Lett.200911(17), 4022–4025. [DOI: 10.1021/ol901745x]

14. Chruma,J. J.;* Moon,S.-J.; Sanford,W. E., Jr. "Azaphilone a-Bromoacetates (AzaBs): Fluorescent Linchpin Reagents for the Inter- and Intramolecular Cross-Linkage of Primary Amines to Thiols," Lett. Org. Chem.20096(5), 367–371.

15. Fields,W. H.;Khan, A. K.; Sabat, M.;Chruma, J. J.* "One-Pot Tandem Decarboxylative Allylation–Heck Cyclization of Allyl Diphenylglycinate Imines: Rapid Access to Polyfunctionalized 1-Aminoindanes", Org. Lett.200810(22), 5131–5134. [DOI: 10.1021/ol801986m]

16. Yeagley, A. A.;Chruma. J. J.* "C–C bond-forming reactions via Pd-mediated decarboxylative a-imino anion generation", Org. Lett.20079(15), 2879–2882. [DOI: 10.1021/ol071080f]

17. Chruma,J. J.; Liu, L.; Zhou, W.; Breslow, R.* "Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics", Bioorg. Med. Chem.200513, 5873-5883. [DOI: 10.1016/j.bmc.2005.05.019]

18. Zhou, W.; Yerkes, N.;Chruma,J. J.; Liu,L.; Breslow, R.* "Chiral polyamines from reduction of polypeptides: asymmetric pyridoxamine-mediated transaminations", Bioorg. Med. Chem. Lett.200515(5), 1351-1355. [DOI: 10.1016/j.bmcl.2005.01.021]

19. Liu, L.; Zhou, W.;Chruma,J.; Breslow, R.* "Transamination reactions with multiple turnovers catalyzed by hydrophobic pyridoxamine cofactors in the presence of polyethylene-imine polymers", J. Am. Chem. Soc.2004126(26), 8136-8137. [DOI: 10.1021/ja048671a]

20. Si, Z.; Madani, N.; Cox, J. M.;Chruma,J. J.; Klein, J. C.; Sch?n, A.; Phan, N.; Wang, L.; Biorn, A. C.; Cocklin, S.; Chaiken, I.; Freire, E.; Smith, A. B., III; Sodroski, J. G.* "Small-molecule inhibitors of HIV-1 entry block receptor-induced conformational changes in the viral envelope glycoproteins", Proc. Nat. Acad. Sci. USA2004101(14), 5036-5041. [DOI: 10.1073/pnas.0307953101]

21. Madani, N.; Perdigoto, A. L.; Srinivasan, K.; Cox, J. M.;Chruma,J. J.; LaLonde, J.; Head, M.; Smith, A. B., III; Sodroski, J. G.* "Localized changes in the gp120 envelope glycoprotein confer resistance to human immunodeficiency virus entry inhibitors BMS-806 and #155", J. Virol.200478(7), 3742-3752. [DOI: 10.1128/JVI.78.7.3742-3752.2004]

22. Smith, A. B. III;* Chruma,J. J.; Han, Q.; Barbosa, J. "Complestatin synthetic studies: the effect of the amino acid configuration on peptide backbone conformation in the common western BCD macrocycle", Bioorg. Med. Chem. Lett.,200414, 1697-1702. [DOI: 10.1016/j.bmcl.2004.01.056]

23. Polt,R.;* Sames, D.;Chruma,J."Glycoside inhibitors: synthesis of enantiomerically pure aza-sugars from Schiff base amino esters via tandem reduction-alkenylation and osmylation", J. Org. Chem.199964(17), 6147-6158. [DOI: 10.1021/jo9820115]

24. Chruma,J. J.; Sames, D.; Polt, R.* "General method for the synthesis of N–methyl amino acids and N–alkylated amino esters from O'Donnell's Schiff base", Tetrahedron Lett.199738(29), 5085-5086. [DOI: 10.1016/S0040-4039(97)01132-5]

ChrumaCV2017_09_14.pdf