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Shenvi, Ryan
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Shenvi, Ryan

Associate Professor
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Positions

  • 2014 - Associate Professor, Chemistry , Scripps Research
  • 2010 - Faculty Member, Skaggs Graduate School of Chemical and Biological Sciences , Scripps Research
  • 2010 - 2014 Assistant Professor, Chemistry , Scripps Research
  • 2008 - 2010 NIH Postdoctoral Fellow with Dr. E.J. Corey, Harvard University
Dr. Shenvi develops chemistry to solve broad problems in complex molecule synthesis, and answers fundamental questions of organic chemistry, with an emphasis on natural products and the invention of new chemical methods.

Research Areas research areas

  • Biochemistry, Genetics and Molecular Biology
  • Chemical Engineering
  • Chemistry (LCSH)
  • Materials Science
  • Medicine
  • Pharmacology, Toxicology and Pharmaceutics

Contact

  • rshenvi@scripps.edu

Websites

  • Ryan Shenvi, Ph.D.
  • Shenvi Laboratory
  • Doctoral Dissertation
  • Twitter @Shenvi_Lab
  • Publications
  • Research
  • Teaching
  • Background
  • Contact
  • Identity
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Publications

recent publications
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  • Publications without PubMed PMIDs

  • academic article

    • Matos, J. L. M., Green, S. A., Chun, Y. G., Dang, V. Q., Dushin, R. G., Richardson, P., Chen, J. S., Piotrowski, D. W., Paegel, B. M., Shenvi, R. A. Cycloisomerization of Olefins in Water Angewandte Chemie-International Edition  2020  DOI:10.1002/anie.202003948  PMID:32285542
    • Crossley, S. W. M., Tong, G. H., Lambrecht, M. J., Burdge, H. E., Shenvi, R. A. Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation Journal of the American Chemical Society  2020 142:11376-11381  DOI:10.1021/jacs.0c05042  PMID:32573211
    • Huffman, B. J., Chen, S., Schwarz, J. L., Plata, R. E., Chin, E. N., Lairson, L. L., Houk, K. N., Shenvi, R. A. Electronic complementarity permits hindered butenolide heterodimerization and discovery of novel cGAS/STING pathway antagonists Nature Chemistry  2020 12:310-317  DOI:10.1038/s41557-019-0413-8  PMID:32042135
    • Baker, M. A.*, Demoret, R. M.*, Ohtawa, M., Shenvi, R. A. Concise asymmetric synthesis of (-)-bilobalide Nature  2019 575:643-646  DOI:10.1038/s41586-019-1690-5  PMID:31618759 (* = equal contribution)
    • Flood, D. T., Asai, S., Zhang, X., Wang, J., Yoon, L., Adams, Z. C., Dillingham, B. C., Sanchez, B. B., Vantourout, J. C., Flanagan, M. E., Piotrowsld, D. W., Richardson, P., et al. Expanding reactivity in DNA-encoded library synthesis via reversible binding of DNA to an inert quaternary ammonium support Journal of the American Chemical Society  2019 141:9998-10006  DOI:10.1021/jacs.9b03774  PMID:31136164
    • Martinez, R. M., Burdge, H. E., Shenvi, R. A. Reanalysis of lindenatriene, a building block for the synthesis of lindenane oligomers Tetrahedron  2019 75:3140-3144  DOI:10.1016/j.tet.2019.03.011
    • Green, S. A., Huffman, T. R., McCourt, R. O., van der Puyl, V., Shenvi, R. A. Hydroalkylation of olefins to form quaternary carbons Journal of the American Chemical Society  2019 141:7709-7714  DOI:10.1021/jacs.9b02844  PMID:31030508
    • Huffman, B. J., Shenvi, R. A. Natural products in the "marketplace": Interfacing synthesis and biology Journal of the American Chemical Society  2019 141:3332-3346  DOI:10.1021/jacs.8b11297  PMID:30682249
    • Huffman, T. R., Wu, Y., Emmerich, A., Shenvi, R. A. Intermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates Angewandte Chemie-International Edition  2019 58:2371-2376  DOI:10.1002/anie.201813233  PMID:30602064  PMCID:PMC6370521
    • Shenvi, R. A., Rodriguez, R., Seitz, O. Tetrahedron Young Investigator Awards Angewandte Chemie-International Edition  2019 58:663-663  DOI:10.1002/anie.201812944
    • Matos, J. L. M., Vasquez-Cespedes, S., Gu, J., Oguma, T., Shenvi, R. A. Branch-selective addition of unactivated olefins into imines and aldehydes Journal of the American Chemical Society  2018 140:16976-16981  DOI:10.1021/jacs.8b11699  PMID:30463404
    • Green, S. A., Crossley, S. W. M., Matos, J. L. M., Vasquez-Cespedes, S., Shevick, S. L., Shenvi, R. A. The high chemofidelity of metal-catalyzed hydrogen atom transfer Accounts of Chemical Research  2018 51:2628-2640  DOI:10.1021/acs.accounts.8b00337  PMID:30406655  PMCID:PMC6248883
    • Shevick, S. L., Obradors, C., Shenvi, R. A. Mechanistic interrogation of Co/Ni-dual catalyzed hydroarylation Journal of the American Chemical Society  2018 140:12056-12068  DOI:10.1021/jacs.8b06458  PMID:30153002
    • Green, S. A., Vasquez-Cespedes, S., Shenvi, R. A. Iron-nickel dual-catalysis: a new engine for olefin functionalization and the formation of quaternary centers Journal of the American Chemical Society  2018 140:11317-11324  DOI:10.1021/jacs.8b05868  PMID:30048124
    • Hirasawa, S., Cho, M., Brust, T. F., Roach, J. J., Bohn, L. M., Shenvi, R. A. O6C-20-nor-salvinorin A is a stable and potent KOR agonist Bioorganic & Medicinal Chemistry Letters  2018 28:2770-2772  DOI:10.1016/j.bmcl.2018.01.055  PMID:29426768  PMCID:PMC6067998
    • Witkin, J. M., Shenvi, R. A., Li, X., Gleason, S. D., Weiss, J., Morrow, D., Catow, J. T., Wakulchik, M., Ohtawa, M., Lu, H. H., Martinez, M. D., Schkeryantz, J. M., et al. Pharmacological characterization of the neurotrophic sesquiterpene jiadifenolide reveals a non-convulsant signature and potential for progression in neurodegenerative disease studies Biochemical Pharmacology  2018 155:61-70  DOI:10.1016/j.bcp.2018.06.022  PMID:29940173  PMCID:PMC6135676
    • Roach, J. J., Shenvi, R. A. A review of salvinorin analogs and their kappa-opioid receptor activity Bioorganic & Medicinal Chemistry Letters  2018 28:1436-1445  DOI:10.1016/j.bmcl.2018.03.029  PMID:29615341  PMCID:PMC5912166
    • Lambrecht, M. J., Kelly, J. W., Shenvi, R. A. Mechanism of action of the cytotoxic asmarine alkaloids ACS Chemical Biology  2018 13:1299-1306  DOI:10.1021/acschembio.8b00096  PMID:29653046  PMCID:PMC5959788
    • Roach, J. J., Sasano, Y., Schmid, C. L., Zaidi, S., Katritch, V., Stevens, R. C., Bohn, L. M., Shenvi, R. A. Dynamic strategic bond analysis yields a ten-step synthesis of 20-nor-salvinorin A, a potent κ-OR agonist ACS Central Science  2017 3:1329-1336  DOI:10.1021/acscentsci.7b00488  PMID:29296674  PMCID:PMC5746855
    • Ohtawa, M., Krambis, M. J., Cerne, R., Schkeryantz, J. M., Witkin, J. M., Shenvi, R. A. Synthesis of (-)-11-O-debenzoyltashironin: neurotrophic sesquiterpenes cause hyperexcitation Journal of the American Chemical Society  2017 139:9637-9644  DOI:10.1021/jacs.7b04206  PMID:28644021
    • Reiher, C. A., Shenvi, R. A. Stereocontrolled synthesis of kalihinol C Journal of the American Chemical Society  2017 139:3647-3650  DOI:10.1021/jacs.7b01124  PMID:28252949
    • Green, S. A., Matos, J. L. M., Yagi, A., Shenvi, R. A. Branch-selective hydroarylation: iodoarene-olefin cross-coupling Journal of the American Chemical Society  2016 138:12779-12782  DOI:10.1021/jacs.6b08507  PMID:27623023
    • Crossley, S. W. M., Obradors, C., Martinez, R. M., Shenvi, R. A. Mn-, Fe-, and Co-catalyzed radical hydrofunctionalizations of olefins Chemical Reviews  2016 116:8912-9000  DOI:10.1021/acs.chemrev.6b00334  PMID:27461578
    • Tada, N., Jansen, D. J., Mower, M. P., Blewett, M. M., Umotoy, J. C., Cravatt, B. F., Wolan, D. W., Shenvi, R. A. Synthesis and sulfur electrophilicity of the Nuphar thiaspirane pharmacophore ACS Central Science  2016 2:401-408  DOI:10.1021/acscentsci.6b00113  PMID:27413784  PMCID:PMC4919772
    • Lu, H. H., Pronin, S. V., Antonova-Koch, Y., Meister, S., Winzeler, E. A., Shenvi, R. A. Synthesis of (+)-7,20-diisocyanoadociane and liver -stage antiplasmodial activity of the isocyanoterpene class Journal of the American Chemical Society  2016 138:7268-7271  DOI:10.1021/jacs.6b03899  PMID:27244042
    • Crossley, S. W. M., Martinez, R. M., Guevara-Zuluaga, S., Shenvi, R. A. Synthesis of the privileged 8-arylmenthol class by radical arylation of isopulegol Organic Letters  2016 18:2620-2623  DOI:10.1021/acs.orglett.6b01047  PMID:27175746
    • Wan, K. K., Shenvi, R. A. Conjuring a supernatural product - DelMarine Synlett  2016 27:1145-1164  DOI:10.1055/s-0035-1561329
    • Obradors, C., Martinez, R. M., Shenvi, R. A. Ph(i-PrO)SiH2: An exceptional reductant for metal-catalyzed hydrogen atom transfers Journal of the American Chemical Society  2016 138:4962-4971  DOI:10.1021/jacs.6b02032  PMID:26984323  PMCID:PMC4858193
    • Shenvi, R. A. Cluster preface: Reinventing radical reactions Synlett  2016 27:678-679  DOI:10.1055/s-0035-1561221
    • Shenvi, R. A. Neurite outgrowth enhancement by jiadifenolide: possible targets Natural Product Reports  2016 33:535-539  DOI:10.1039/c5np00160a  PMID:26891462
    • Tabor, M. G., Shenvi, R. A. Synthesis of lepadiformine using a hydroamination transform Organic Letters  2015 17:5776-5779  DOI:10.1021/acs.orglett.5b02992  PMID:26584132
    • Crossley, S. W. M., Shenvi, R. A. A longitudinal study of alkaloid synthesis reveals functional group interconversions as bad actors Chemical Reviews  2015 115:9465-9531  DOI:10.1021/acs.chemrev.5b00154  PMID:26158529
    • Lu, H. H., Martinez, M. D., Shenvi, R. A. An eight-step gram-scale synthesis of (-)-jiadifenolide Nature Chemistry  2015 7:604-607  DOI:10.1038/nchem.2283  PMID:26100810
    • Roach, J. J., Shenvi, R. A. Supramolecular catalysis: Terpenes in tight spaces Nature Chemistry  2015 7:187-189  DOI:10.1038/nchem.2191  PMID:25698322
    • Wan, K. K., Iwasaki, K., Umotoy, J. C., Wolan, D. W., Shenvi, R. A. Nitrosopurines en route to potently cytotoxic asmarines Angewandte Chemie-International Edition  2015 54:2410-2415  DOI:10.1002/anie.201411493  PMID:25580910  PMCID:PMC4470469
    • Bach, T., Shenvi, R. A., Weix, D. J., Giralt, E., Schwarz, H. Honda-Fujishima Lectureship Award for Thorsten Bach Angewandte Chemie-International Edition  2015 54:2003-2003  DOI:10.1002/anie.201412056
    • Schnermann, M. J., Shenvi, R. A. Syntheses and biological studies of marine terpenoids derived from inorganic cyanide Natural Product Reports  2015 32:543-577  DOI:10.1039/c4np00109e  PMID:25514696  PMCID:PMC4414506
    • Crossley, S. W. M., Barabe, F., Shenvi, R. A. Simple, chemoselective, catalytic olefin isomerization Journal of the American Chemical Society  2014 136:16788-16791  DOI:10.1021/ja5105602  PMID:25398144  PMCID:PMC4277770
    • Iwasaki, K., Wan, K. K., Oppedisano, A., Crossley, S. W. M., Shenvi, R. A. Simple, chemoselective hydrogenation with thermodynamic stereocontrol Journal of the American Chemical Society  2014 136:1300-1303  DOI:10.1021/ja412342g  PMID:24428640  PMCID:PMC3951266
    • Jansen, D. J., Shenvi, R. A. Synthesis of medicinally relevant terpenes: reducing the cost and time of drug discovery Future Medicinal Chemistry  2014 6:1127-1146  DOI:10.4155/fmc.14.71  PMID:25078134  PMCID:PMC4162426
    • Shenvi, R. A., Pronin, S. V. Synthesis of highly strained terpenes by non-stop tail-to-head polycyclization Synthesis-Stuttgart  2013 45:A19-A20  DOI:10.1055/s-003-24382  PMID:23089866
    • Jansen, D. J., Shenvi, R. A. Synthesis of (-)-neothiobinupharidine Journal of the American Chemical Society  2013 135:1209-1212  DOI:10.1021/ja310778t  PMID:23298203
    • Pronin, S. V., Reiher, C. A., Shenvi, R. A. Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines Nature  2013 501:195-199  DOI:10.1038/nature12472  PMID:24025839
    • Pronin, S. V., Shenvi, R. A. Synthesis of a potent antimalarial amphilectene Journal of the American Chemical Society  2012 134:19604-19606  DOI:10.1021/0310129b  PMID:23153381
    • Pronin, S. V., Shenvi, R. A. Synthesis of highly strained terpenes by non-stop tail-to-head polycyclization Nature Chemistry  2012 4:915-920  DOI:10.1038/nchem.1458  PMID:23089866
    • Pronin, S. V., Tabor, M. G., Jansen, D. J., Shenvi, R. A. A stereoselective hydroamination transform to access polysubstituted indolizidines Journal of the American Chemical Society  2012 134:2012-2015  DOI:10.1021/ja211090n  PMID:22263967
    • degree-related publication Shi, J., Manolikakes, G., Yeh, C. H., Guerrero, C. A., Shenvi, R. A., Shigehisa, H., Baran, P. S. Scalable synthesis of cortistatin A and related structures Journal of the American Chemical Society  2011 133:8014-8027  DOI:10.1021/ja202103e  PMID:21539314  PMCID:PMC3119343
    • Shenvi, R. A., Corey, E. J. Synthetic access to bent polycycles by cation-pi cyclization Organic Letters  2010 12:3548-3551  DOI:10.1021/ol101410g  PMID:20670018  PMCID:PMC2914341
    • Shenvi, R. A., Corey, E. J. A short and efficient synthesis of (-)-7-methylomuralide, a potent proteasome inhibitor Journal of the American Chemical Society  2009 131:5746-5747  DOI:10.1021/ja901400q  PMID:19338298  PMCID:PMC2714661
    • degree-related publication Shenvi, R. A., O'Malley, D. P., Baran, P. S. Chemoselectivity: The mother of invention in total synthesis Accounts of Chemical Research  2009 42:530-541  DOI:10.1021/ar800182r  PMID:19182997  PMCID:PMC2765532
    • degree-related publication Shi, J., Shigehisa, H., Guerrero, C. A., Shenvi, R. A., Li, C. C., Baran, P. S. Stereodivergent synthesis of 17-alpha and 17-beta-alpharyl steroids: Application and biological evaluation of D-ring cortistatin analogues Angewandte Chemie-International Edition  2009 48:4328-4331  DOI:10.1002/anie.200901116  PMID:19434636  PMCID:PMC3495592
    • degree-related publication Shenvi, R. A., Guerrero, C. A., Shi, J., Li, C. C., Baran, P. S. Synthesis of (+)-cortistatin A Journal of the American Chemical Society  2008 130:7241-7243  DOI:10.1021/ja8023466  PMID:18479104  PMCID:PMC2652360
    • degree-related publication Baran, P. S., Shenvi, R. A., Nguyen, S. A. One-step synthesis of 4,5-disubstituted pyrimidines using commercially available and inexpensive reagents Heterocycles  2006 70:581-586  DOI:10.3987/COM-06-S(W)27
    • degree-related publication Baran, P. S., Shenvi, R. A. Total synthesis of (+/-)-chartelline C Journal of the American Chemical Society  2006 128:14028-14029  DOI:10.1021/ja0659673  PMID:17061876
    • degree-related publication Baran, P. S., Shenvi, R. A., Mitsos, C. A. A remarkable ring contraction en route to the chartelline alkaloids Angewandte Chemie-International Edition  2005 44:3714-3717  DOI:10.1002/anie.200500522  PMID:15900528
    • Ababou, A., Shenvi, R. A., Desjarlais, J. R. Long-range effects on calcium binding and conformational change in the n-domain of calmodulin Biochemistry  2001 40:12719-12726  DOI:10.1021/bi010405b  PMID:11601997

featured in

  • Scripps Research Institute Scientists Solve Century-Old Chemistry Problem  News Release
  • TSRI Chemists’ Work Selected Among Most Significant in 2013  Newsletter
  • Unexpected Turnabout For Tertiary Alcohols  Article
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Research

research overview

  • Synthetic Organic Chemistry

    Secondary metabolites constitute a vast and largely unexplored library of complex molecular architecture unlike anything man has the capacity to create. Useful for target identification, initial lead development, clinical study, and occasionally prescription, natural products are projected to continue as central players in the treatment of human pathologies.

    Nevertheless, the complexity inherent to these molecules has often had a prohibitive effect on their inclusion in traditional medicinal chemistry.

    Our lab seeks to address some of the issues at the heart of this problem, within the context of particular structural motifs and secondary metabolite subclasses. A multi-factorial approach to problem solving is operative in our research, comprising the exploration of chemical reactivity, invention of strategies and concepts for complex molecule synthesis, and expansion of the tools available to synthetic chemists.

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Teaching

advisees

  • graduate advising relationship

    • Baker, Meghan Amanda, Ph.D.  candidate, 2017 -
    • Demoret, Rob, Ph.D.  candidate, 2016 -
    • Green, Samantha, Ph.D.  candidate, 2016 -
    • Hill, Sarah Jane, Ph.D.  candidate, 2019 -
    • Huffman, Benjamin James, Ph.D.  candidate, 2016 -
    • Huffman, Tucker Ryan, Ph.D.  candidate, 2018 -
    • Shevick, Sophia, Ph.D.  candidate, 2017 -
    • Van Der Puyl, Vincent Andrew, Ph.D.  candidate, 2019 -
    • Burdge, Hannah, Ph.D.  candidate, 2018 - 2019
    • Melendez-Matos, Jeishla, Ph.D.  candidate, 2015 - 2019
    • Crossley, Steven, Ph.D.  candidate, 2014 - 2018
    • Martinez, Ruben Martin, Ph.D.  candidate, 2014 - 2018
    • Roach, Jeremy, Ph.D.  candidate, 2013 - 2018
    • Reiher, Chris, Ph.D.  candidate, 2013 - 2017
    • Jansen, Dan, Ph.D.  candidate, 2011 - 2015
    • Tabor, Greg Martin , Ph.D.  candidate, 2011 - 2015
    • Wan, Kanny, Ph.D.  candidate, 2012 - 2015
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Background

education and training

  • Ph.D. in Chemistry, Scripps Research 2003 - 2008
  • B.S. in Chemistry, The Pennsylvania State University , with Dr. R. L. Funk 1999 - 2003

awards and honors

  • Tetrahedron Young Investigator Awards, 2019
  • NPR Emerging Investigator, conferred by Royal Society of Chemistry, 2016
  • Eli Lilly Grantee Award, conferred by Eli Lilly & Company, 2015
  • Novartis Early Career Award, conferred by Genomics Institute of the Novartis Research Foundation, 2014
  • Bristol-Myers Squibb Grant in Synthetic Organic Chemistry, conferred by Bristol-Myers Squibb, 2014
  • Sloan Research Fellowship, conferred by Alfred P. Sloan Foundation, 2014
  • NSF Career Award, conferred by National Science Foundation, 2013
  • Baxter Young Investigator Award, conferred by Baxter, 2013
  • Amgen Young Investigator Award, conferred by Amgen, 2013
  • Thieme Chemistry Journal Award, conferred by Thieme Chemistry, 2012
  • Boehringer-Ingelheim Young Investigator Award, conferred by Boehringer Ingelheim, 2012
  • Eli Lilly New Faculty Award, conferred by Eli Lilly & Company, 2011

advisee of

  • graduate advising relationship

    • Baran, Phil, Ph.D.  candidacy, 2004 - 2008
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Contact

full name

  • Ryan Shenvi

geographic location

  • Scripps California 
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Identity

ORCID iD

  • ORCID iD http://orcid.org/0000-0001-8353-6449

Scopus ID

  • 8567630000

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