Christopher D. Vanderwal - Publications

Affiliations: 
Chemistry University of California, Irvine, Irvine, CA 
Area:
Organic and Synthetic
Website:
http://www.faculty.uci.edu/profile.cfm?faculty_id=5265

60 high-probability publications. We are testing a new system for linking publications to authors. You can help! If you notice any inaccuracies, please sign in and mark papers as correct or incorrect matches. If you identify any major omissions or other inaccuracies in the publication list, please let us know.

Year Citation  Score
2019 Balaguer FA, Mühlethaler T, Estévez-Gallego J, Calvo E, Giménez-Abián JF, Risinger AL, Sorensen EJ, Vanderwal CD, Altmann KH, Mooberry SL, Steinmetz MO, Oliva MÁ, Prota AE, Díaz JF. Crystal Structure of the Cyclostreptin-Tubulin Adduct: Implications for Tubulin Activation by Taxane-Site Ligands. International Journal of Molecular Sciences. 20. PMID 30897704 DOI: 10.3390/ijms20061392  1
2017 Schwarzwalder GM, Vanderwal CD. Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products. European Journal of Organic Chemistry. 2017: 1567-1577. PMID 29527124 DOI: 10.1002/ejoc.201601418  0.32
2016 Schwarzwalder GM, Scott DR, Vanderwal CD. A Synthesis of Exiguaquinol Dessulfate. Chemistry (Weinheim An Der Bergstrasse, Germany). PMID 27673578 DOI: 10.1002/chem.201604506  0.32
2016 White AR, Duggan BM, Tsai SC, Vanderwal CD. The Alga Ochromonas danica Produces Bromosulfolipids. Organic Letters. PMID 26889956 DOI: 10.1021/acs.orglett.6b00230  1
2016 Horn EJ, Silverston JS, Vanderwal CD. A Failed Late-Stage Epimerization Thwarts an Approach to Ineleganolide. The Journal of Organic Chemistry. PMID 26863401 DOI: 10.1021/acs.joc.5b02550  1
2016 Chung WJ, Vanderwal CD. Stereoselective Halogenation in Natural Product Synthesis. Angewandte Chemie (International Ed. in English). PMID 26833878 DOI: 10.1002/anie.201506388  1
2015 Quinn RK, Könst ZA, Michalak SE, Schmidt Y, Szklarski AR, Flores AR, Nam S, Horne DA, Vanderwal CD, Alexanian EJ. Site-Selective Aliphatic C-H Chlorination Using N-Chloroamides Enables a Synthesis of Chlorolissoclimide. Journal of the American Chemical Society. PMID 26694767 DOI: 10.1021/jacs.5b12308  1
2015 Hong AY, Vanderwal CD. A Synthesis of Alsmaphorazine B Demonstrates the Chemical Feasibility of a New Biogenetic Hypothesis. Journal of the American Chemical Society. 137: 7306-9. PMID 26034815 DOI: 10.1021/jacs.5b04686  1
2015 Pham HV, Karns AS, Vanderwal CD, Houk KN. Computational and experimental investigations of the formal dyotropic rearrangements of himbert arene/allene cycloadducts. Journal of the American Chemical Society. 137: 6956-64. PMID 25961134 DOI: 10.1021/jacs.5b03718  1
2015 Daub ME, Prudhomme J, Le Roch K, Vanderwal CD. Synthesis and potent antimalarial activity of kalihinol B. Journal of the American Chemical Society. 137: 4912-5. PMID 25815413 DOI: 10.1021/jacs.5b01152  1
2015 Romonosky DE, Nguyen LQ, Shemesh D, Nguyen TB, Epstein SA, Martin DBC, Vanderwal CD, Gerber RB, Nizkorodov SA. Absorption spectra and aqueous photochemistry of β-hydroxyalkyl nitrates of atmospheric interest Molecular Physics. DOI: 10.1080/00268976.2015.1017020  1
2014 Atwood BR, Vanderwal CD. Synthetic methodology: catalytic control of chlorination. Nature Chemistry. 7: 99-100. PMID 25615661 DOI: 10.1038/nchem.2163  1
2014 Vogel CV, Pietraszkiewicz H, Sabry OM, Gerwick WH, Valeriote FA, Vanderwal CD. Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors. Angewandte Chemie (International Ed. in English). 53: 12205-9. PMID 25220828 DOI: 10.1002/anie.201407726  1
2014 Roosen PC, Vanderwal CD. Investigations into an anionic oxy-cope/transannular conjugate addition approach to 7,20-diisocyanoadociane. Organic Letters. 16: 4368-71. PMID 25105694 DOI: 10.1021/ol502205m  1
2014 Tartakoff SS, Vanderwal CD. A synthesis of the ABC tricyclic core of the clionastatins serves to corroborate their proposed structures. Organic Letters. 16: 1458-61. PMID 24571064 DOI: 10.1021/ol500265v  1
2014 Chung WJ, Carlson JS, Vanderwal CD. General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form. The Journal of Organic Chemistry. 79: 2226-41. PMID 24494597 DOI: 10.1021/jo5000829  1
2014 Chung WJ, Vanderwal CD. Approaches to the chemical synthesis of the chlorosulfolipids. Accounts of Chemical Research. 47: 718-28. PMID 24400674 DOI: 10.1021/ar400246w  1
2014 Lam JK, Joseph SB, Vanderwal CD. A Zincke aldehyde approach to gelsemine Tetrahedron Letters. 56: 3165-3168. DOI: 10.1016/j.tetlet.2014.12.089  1
2013 Schwarzwalder GM, Steinhardt SE, Pham HV, Houk KN, Vanderwal CD. Synthesis of the tetracyclic core of exiguaquinol. Organic Letters. 15: 6014-7. PMID 24219829 DOI: 10.1021/ol402905n  1
2013 Lam JK, Pham HV, Houk KN, Vanderwal CD. Computation and experiment reveal that the ring-rearrangement metathesis of Himbert cycloadducts can be subject to kinetic or thermodynamic control. Journal of the American Chemical Society. 135: 17585-94. PMID 24111571 DOI: 10.1021/ja409618p  1
2013 Chung WJ, Carlson JS, Bedke DK, Vanderwal CD. A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps. Angewandte Chemie (International Ed. in English). 52: 10052-5. PMID 23929596 DOI: 10.1002/anie.201304565  1
2013 Schmidt Y, Lam JK, Pham HV, Houk KN, Vanderwal CD. Studies on the Himbert intramolecular arene/allene Diels-Alder cycloaddition. Mechanistic studies and expansion of scope to all-carbon tethers. Journal of the American Chemical Society. 135: 7339-48. PMID 23634642 DOI: 10.1021/ja4025963  1
2012 Lam JK, Schmidt Y, Vanderwal CD. Complex polycyclic scaffolds by metathesis rearrangement of Himbert arene/allene cycloadducts. Organic Letters. 14: 5566-9. PMID 23067058 DOI: 10.1021/ol302680m  1
2012 Michels TD, Dowling MS, Vanderwal CD. A synthesis of echinopine B. Angewandte Chemie (International Ed. in English). 51: 7572-6. PMID 22711188 DOI: 10.1002/anie.201203147  1
2012 Pham HV, Martin DB, Vanderwal CD, Houk KN. The Intramolecular Diels-Alder Reaction of Tryptamine-Derived Zincke Aldehydes Is a Stepwise Process. Chemical Science (Royal Society of Chemistry : 2010). 2012: 1650-1655. PMID 22611483 DOI: 10.1039/C2SC01072K  1
2012 Martin DB, Nguyen LQ, Vanderwal CD. Syntheses of strychnine, norfluorocurarine, dehydrodesacetylretuline, and valparicine enabled by intramolecular cycloadditions of Zincke aldehydes. The Journal of Organic Chemistry. 77: 17-46. PMID 22168233 DOI: 10.1021/jo2020246  1
2012 Calvo E, Barasoain I, Matesanz R, Pera B, Camafeita E, Pineda O, Hamel E, Vanderwal CD, Andreu JM, López JA, Díaz JF. Cyclostreptin derivatives specifically target cellular tubulin and further map the paclitaxel site. Biochemistry. 51: 329-41. PMID 22148836 DOI: 10.1021/bi201380p  1
2012 Martin DBC, Vanderwal CD. A short synthesis of strychnine from pyridine Total Synthesis of Natural Products: At the Frontiers of Organic Chemistry. 2147483647: 67-102. DOI: 10.1007/978-3-642-34065-9_4  1
2011 Vanderwal CD. Reactivity and synthesis inspired by the Zincke ring-opening of pyridines. The Journal of Organic Chemistry. 76: 9555-67. PMID 21877712 DOI: 10.1021/jo201625e  1
2011 Paton RS, Steinhardt SE, Vanderwal CD, Houk KN. Unraveling the mechanism of cascade reactions of zincke aldehydes. Journal of the American Chemical Society. 133: 3895-905. PMID 21351736 DOI: 10.1021/ja107988b  1
2011 Bedke DK, Vanderwal CD. Chlorosulfolipids: structure, synthesis, and biological relevance. Natural Product Reports. 28: 15-25. PMID 21125121 DOI: 10.1039/c0np00044b  1
2011 Martin DBC, Vanderwal CD. A synthesis of strychnine by a longest linear sequence of six steps Chemical Science. 2: 649-651. DOI: 10.1039/c1sc00009h  1
2010 Steinhardt SE, Vanderwal CD. Synthetic strategy: without a trace. Nature Chemistry. 2: 254-6. PMID 21124503 DOI: 10.1038/nchem.602  1
2010 Dowling MS, Vanderwal CD. Ring-closing metathesis of allylsilanes as a flexible strategy toward cyclic terpenes. short syntheses of teucladiol, isoteucladiol, poitediol, and dactylol and an attempted synthesis of caryophyllene. The Journal of Organic Chemistry. 75: 6908-22. PMID 20836562 DOI: 10.1021/jo101439h  1
2010 Michels TD, Kier MJ, Kearney AM, Vanderwal CD. Concise formal synthesis of porothramycins A and B via Zincke pyridinium ring-opening/ring-closing cascade. Organic Letters. 12: 3093-5. PMID 20527899 DOI: 10.1021/ol101035p  1
2010 Martin DB, Vanderwal CD. Concise synthesis of (-)-nakadomarin A. Angewandte Chemie (International Ed. in English). 49: 2830-2. PMID 20301158 DOI: 10.1002/anie.201000045  1
2010 Bedke DK, Shibuya GM, Pereira AR, Gerwick WH, Vanderwal CD. A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A. Journal of the American Chemical Society. 132: 2542-3. PMID 20141139 DOI: 10.1021/ja910809c  1
2010 Pereira AR, Byrum T, Shibuya GM, Vanderwal CD, Gerwick WH. Structure revision and absolute configuration of malhamensilipin A from the freshwater chrysophyte Poterioochromonas malhamensis. Journal of Natural Products. 73: 279-83. PMID 20099812 DOI: 10.1021/np900672h  1
2009 Dowling MS, Vanderwal CD. Ring-closing metathesis of allylsilanes/electrophilic desilylation to prepare exo-methylidenecycloalkanes. Short syntheses of teucladiol and poitediol. Journal of the American Chemical Society. 131: 15090-1. PMID 19788178 DOI: 10.1021/ja906241w  1
2009 Steinhardt SE, Vanderwal CD. Complex polycyclic lactams from pericyclic cascade reactions of Zincke aldehydes. Journal of the American Chemical Society. 131: 7546-7. PMID 19449870 DOI: 10.1021/ja902439f  1
2009 Bedke DK, Shibuya GM, Pereira A, Gerwick WH, Haines TH, Vanderwal CD. Relative stereochemistry determination and synthesis of the major chlorosulfolipid from Ochromonas danica. Journal of the American Chemical Society. 131: 7570-2. PMID 19445461 DOI: 10.1021/ja902138w  1
2009 Martin DB, Vanderwal CD. Efficient access to the core of the Strychnos, Aspidosperma and Iboga alkaloids. A short synthesis of norfluorocurarine. Journal of the American Chemical Society. 131: 3472-3. PMID 19236094 DOI: 10.1021/ja900640v  1
2009 Bedke DK, Vanderwal CD. Organic chemistry: Chlorine lends a helping hand. Nature. 457: 548-9. PMID 19177122 DOI: 10.1038/457548a  1
2009 Kanady JS, Nguyen JD, Ziller JW, Vanderwal CD. Synthesis and characterization of all four diastereomers of 3,4-dichloro-2-pentanol, motifs relevant to the chlorosulfolipids. The Journal of Organic Chemistry. 74: 2175-8. PMID 19161314 DOI: 10.1021/jo802390e  1
2008 Michels TD, Rhee JU, Vanderwal CD. Synthesis of delta-tributylstannyl-alpha,beta,gamma,delta-unsaturated aldehydes from pyridines. Organic Letters. 10: 4787-90. PMID 18817407 DOI: 10.1021/ol8020435  1
2008 Shibuya GM, Kanady JS, Vanderwal CD. Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids. Journal of the American Chemical Society. 130: 12514-8. PMID 18717563 DOI: 10.1021/ja804167v  1
2008 Steinhardt SE, Silverston JS, Vanderwal CD. Stereocontrolled synthesis of Z-dienes via an unexpected pericyclic cascade rearrangement of 5-amino-2,4-pentadienals. Journal of the American Chemical Society. 130: 7560-1. PMID 18505251 DOI: 10.1021/ja8028125  1
2008 Bai R, Vanderwal CD, Díaz JF, Hamel E. Interaction of a cyclostreptin analogue with the microtubule taxoid site: the covalent reaction rapidly follows binding. Journal of Natural Products. 71: 370-4. PMID 18298077 DOI: 10.1021/np800056m  1
2007 Buey RM, Calvo E, Barasoain I, Pineda O, Edler MC, Matesanz R, Cerezo G, Vanderwal CD, Day BW, Sorensen EJ, López JA, Andreu JM, Hamel E, Díaz JF. Cyclostreptin binds covalently to microtubule pores and lumenal taxoid binding sites. Nature Chemical Biology. 3: 117-25. PMID 17206139 DOI: 10.1038/nchembio853  1
2006 Kearney AM, Vanderwal CD. Synthesis of nitrogen heterocycles by the ring opening of pyridinium salts. Angewandte Chemie (International Ed. in English). 45: 7803-6. PMID 17072923 DOI: 10.1002/anie.200602996  1
2005 Edler MC, Buey RM, Gussio R, Marcus AI, Vanderwal CD, Sorensen EJ, Díaz JF, Giannakakou P, Hamel E. Cyclostreptin (FR182877), an antitumor tubulin-polymerizing agent deficient in enhancing tubulin assembly despite its high affinity for the taxoid site. Biochemistry. 44: 11525-38. PMID 16114889 DOI: 10.1021/bi050660m  1
2004 Vanderwal CD, Jacobsen EN. Enantioselective formal hydration of alpha,beta-unsaturated imides by Al-catalyzed conjugate addition of oxime nucleophiles. Journal of the American Chemical Society. 126: 14724-5. PMID 15535689 DOI: 10.1021/ja045563f  1
2004 Vanderwal CD, Sorensen EJ. Chapter 1 A remarkable architectural self-construction process is discovered in a synthesis of FR182877 Strategies and Tactics in Organic Synthesis. 5: 1-50. DOI: 10.1016/S1874-6004(04)80024-8  1
2003 Adam GC, Vanderwal CD, Sorensen EJ, Cravatt BF. (-)-FR182877 is a potent and selective inhibitor of carboxylesterase-1. Angewandte Chemie (International Ed. in English). 42: 5480-4. PMID 14618582 DOI: 10.1002/anie.200352576  1
2003 Vanderwal CD, Vosburg DA, Weiler S, Sorensen EJ. An enantioselective synthesis of FR182877 provides a chemical rationalization of its structure and affords multigram quantities of its direct precursor. Journal of the American Chemical Society. 125: 5393-407. PMID 12720453 DOI: 10.1021/ja021472b  1
2002 Vosburg DA, Vanderwal CD, Sorensen EJ. A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Journal of the American Chemical Society. 124: 4552-3. PMID 11971689 DOI: 10.1021/ja025885o  1
2001 Vanderwal CD, Vosburg DA, Sorensen EJ. Intramolecular allenolate acylations in studies toward a synthesis of FR182877. Organic Letters. 3: 4307-10. PMID 11784204  1
2001 Vanderwal CD, Vosburg DA, Sorensen EJ. Intramolecular allenolate acylations in studies toward a synthesis of FR182877 Organic Letters. 3: 4307-4310. DOI: 10.1021/ol016994v  1
1999 Vanderwal CD, Vosburg DA, Weiler S, Sorensen EJ. Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis. Organic Letters. 1: 645-8. PMID 10823194  1
1996 Friesen RW, Vanderwal C. Total synthesis of (±)-dihydrokawain-5-ol. Regioselective monoprotection of vicinal syn-diols derived from the iodocyclofunctionalization of α-allenic alcohols Journal of Organic Chemistry. 61: 9103-9110. DOI: 10.1021/jo961653u  1
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