Stoltz, Brian M - California Institute of Technology, Caltech - Division of Chemistry and Chemical Engineering

个人简介

B.A., B.S., Indiana University of Pennsylvania, 1993; M.A., Yale University, 1996; Ph.D., 1997. Assistant Professor, Caltech, 2000-06; Associate Professor, 2006-07; Professor, 2007-; Bowles Professor, 2007-12. Executive Officer, 2010-12.

研究领域

Research in the Stoltz group has been initiated in the general area of chemical synthesis with a focus on the development of new strategies for the preparation of complex molecules possessing interesting structural, biological, and physical properties. In concert with the design and development of unique and efficient synthetic strategies, we will develop new techniques and methods which will be useful in far reaching and unanticipated applications, as well as for the synthesis of the initial inspirational target. Thus, the general research paradigm within the Stoltz laboratory will be to utilize architecturally complex target molecules as the driving force behind the development of new reactions, which extend the limits of the science. Ultimately, we will have access to important biologically active compounds prepared through novel and efficient routes, as well as new techniques for the preparation of other structurally unique targets.

近期论文

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Total synthesis of (–)-cylindrocyclophane A facilitated by C–H functionalization. Aaron T. Bosse, Liam R. Hunt, Camila A. Suarez, Tyler D. Casselman, Elizabeth L. Goldstein, Austin C. Wright, Hojoon Park, Scott C. Virgil, Jin-Quan Yu, Brian M. Stoltz, and Huw M. L. Davies. Science 2024, 386, 641–646. Formation of All-Carbon Quaternary Centers via Enantioselective Pd-Catalyzed α-Vinylation of γ-Lactams. Farbod A. Moghadam, Jay P. Barbor, Melinda Chan, Carina Jette, Shunya Sakurai, and Brian M. Stoltz. Org. Lett. 2024, 26, 7551–7554 Enantioselective Nickel-Catalyzed α-Spirocyclization of Lactones. Allison M. Stanko, Melissa Ramirez, Adrian J. de Almenara, Scott C. Virgil, and Brian M. Stoltz. Org. Lett. 2024, 26, 6793–6797. Systematic Route to Construct the 5–5–6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids. Melinda Chan, Nicholas J. Hafeman, Tyler J. Fulton, and Brian M. Stoltz. Org. Lett. 2024, 26, 6320–6323. Total Synthesis of Hypersampsone M. Adrian E. Samkian, Scott C. Virgil, and Brian M. Stoltz. J. Am. Chem. Soc. 2024, 146, 18886–18891. Strategies for the Development of Asymmetric and Non-Directed Petasis Reactions. Kevin J. Gonzalez, Chloe Cerione, and Brian M. Stoltz. Chem. Eur. J. 2024, e202401936. Evolution of a Synthetic Strategy toward the Syntheses of Bis-tetrahydroisoquinoline Alkaloids. Aurapat Ngamnithiporn, Eric R. Welin, Gerit Pototschnig, and Brian M. Stoltz. Acc. Chem. Res. 2024, 57, 1870–1884. Molecular Dynamics Investigations of Dienolate [4 + 2] Reactions. Peng-Jui Chen, Alexander Q. Cusumano, Kaylin N. Flesch, Christian Santiago Strong, William A. Goddard III, and Brian M. Stoltz. J. Am. Chem. Soc. 2024, 146, 12758–12765. Convenient access to a strained bicyclic enone: A concise and improved formal synthesis of ineleganolide. Benjamin M. Gross and Brian M. Stoltz. Tetrahedron Lett. 2024, 140, 155011 Divergent Total Syntheses of Pyrroloiminoquinone Alkaloids Enabled by the Development of a Larock/Buchwald–Hartwig Annulation/Cyclization. Samir P. Rezgui, Jonathan Farhi, Hao Yu, Zachary P. Sercel, Scott C. Virgil, and Brian M. Stoltz. Chem. Sci. 2024, 15, 12284–12290. Enantioselective Total Synthesis of (–)-Hunterine A Enabled by a Desymmetrization/Rearrangement Strategy. Elliot F. Hicks, Kengo Inoue, Brian M. Stoltz. J. Am. Chem. Soc. 2024, 146, 4340-4345. Low Part-Per-Trillion, Humidity Resistant Detection of Nitric Oxide Using Microtoroid Optical Resonators. Yinchao Xu, Allison Stanko, Chloe Cerione, Trevor Lohrey, Euan McLeod, Brian Stoltz, Judith Su. ACS Appl. Mater. Interfaces 2024, 16, 5120–5128. Particle-phase accretion forms dimer esters in pinene secondary organic aerosol. Christopher M. Kenseth, Nicholas J. Hafeman, Samir P. Rezgui, Jing Chen, Yuanlong Huang, Nathan F. Dalleska, Henrik G. Kjaergaard, Brian M. Stoltz, John H. Seinfeld, and Paul O. Wennberg. Science. 2023, 382, 787-792. Total Synthesis of Aleutianamine. Hao Yu, Zachary Sercel, Samir Rezgui, Jonathan Farhi, Scott Virgil, and Brian Stoltz. J. Am. Chem. Soc. 2023, 145, 47, 25533–25537. Origins of Enhanced Enantioselectivity in the Pd-Catalyzed Decarboxylative Allylic Alkylation of N-Benzoyl Lactams. Alexander Q. Cusumano, Tianyi Zhang , William A. Goddard III and Brian M. Stoltz. Catalysts. 2023, 13, 1258. Enantioselective 1,3-Dipolar Cycloadditions of α‑Methylene Lactams to Construct Spirocycles. Yuji Nishiura, Kevin J. Gonzalez, Alexander Q. Cusumano and Brian M. Stoltz. Org. Lett. 2023, 25, 6469–6473. Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Lactams: Enantioselective Construction of All-Carbon Quaternary Stereocenters in Saturated Nitrogen-Containing Heterocycles. Tianyi Zhang, Yuji Nishiura, Alexander Q. Cusumano and Brian M. Stoltz. Org. Lett. 2023, 25, 6479–6484. Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020) Alexia N. Kim, Aurapat Ngamnithiporn, Emily Du, and Brian M. Stoltz. Chem. Rev. 2023, 123, 9447–9496. Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides. Jay P. Barbor, Vaishnavi N. Nair, Kimberly R. Sharp, Trevor D. Lohrey, Sara E. Dibrell, Tejas K. Shah, Martin J. Walsh, Sarah E. Reisman, and Brian M. Stoltz. J. Am. Chem. Soc. 2023, 145, 15071–15077. Tandem Dearomatization/Enantioselective Allylic Alkylation of Pyridines. Steffen Greßies, Lars Süße, Tyler Casselman, and Brian M. Stoltz. J. Am. Chem. Soc. 2023, 145, 11907-11913. Divergent Catalysis: Catalytic Asymmetric [4+2] Cycloaddition of Palladium Enolates. Kaylin N. Flesch*, Alexander Q. Cusumano*, Peng-Jui Chen, Christian Santiago Strong, Stephen R. Sardini, Yun E. Du, Michael D. Bartberger, William A. Goddard III, Brian M. Stoltz. J. Am. Chem. Soc. 2023, 145, 11301–11310. [* denotes equal contribution] Total Synthesis of Strempeliopidine and Non-Natural Stereoisomers through a Convergent Petasis Borono–Mannich Reaction. Alexander W. Rand, Kevin J. Gonzalez, Christopher E. Reimann, Scott C. Virgil, Brian M. Stoltz. J. Am. Chem. Soc. 2023, 145, 7278–7287. [highlighted in OPR&D] Total synthesis of (−)-scabrolide A and (−)-yonarolide. Nicholas J. Hafeman, Steven A. Loskot, Christopher E. Reimann, Beau P. Pritchett, Scott C. Virgil, Brian M. Stoltz. Chem. Sci., 2023, 14, 4745–4758. Accretion Product Formation in the Self-Reaction of Ethene-Derived Hydroxy Peroxy Radicals. Sara Edinger Murphy , John D. Crounse , Kristian H. Møller , Samir Rezgui , Nicholas J Hafeman , James Park , Henrik Kjaergaard , Brian M. Stoltz and Paul O Wennberg. Environ. Sci.: Atmos., 2023, 3, 882–893. A Convergent Total Synthesis of (+)-Ineleganolide. Benjamin M. Gross, Seo-Jung Han, Scott C. Virgil, Brian M. Stoltz. J. Am. Chem. Soc., 2023, 145, 7763–7767. Development of a Non-Directed Petasis-Type Reaction by an Aromaticity-Disrupting Strategy. Kevin J. Gonzalez, Alexander W. Rand, Brian M. Stoltz. Angew. Chem. Int. Ed., 2023, 62, e202218921. What is a cross-coupling? An argument for a universal definition . Christopher E. Reimann, Kelly E. Kim, Alexander W. Rand, Farbod A. Moghadam, and Brian M. Stoltz. Tetrahedron., 2023, 130, 133176. Asymmetric Total Synthesis of Havellockate. Nicholas J. Hafeman*, Melinda Chan*, Tyler J. Fulton, Eric J. Alexy, Steven A. Loskot, Scott. C. Virgil, and Brian M. Stoltz. J. Am. Chem. Soc., 2022, 144, 20232-20236. [* denotes equal contribution] Investigations of an Unexpected [2+2] Photocycloaddition in the Synthesis of (−)-Scabrolide A from Quantum Mechanics Calculations. Tianyi Zhang*, Alexander Q. Cusumano*, Nicholas J. Hafeman, Steven A. Loskot, Christopher E. Reimann, Scott C. Virgil, William A. Goddard III, and Brian M. Stoltz. J. Org. Chem., 2022, 87, 14115-14124. [* denotes equal contribution] Synthesis of enantioenriched 2,2-disubstituted pyrrolidines via sequential asymmetric allylic alkylation and ring contraction. Elizabeth L. Goldstein, Hirokazu Takada, Yuji Sumii, Katsuaki Baba, Brian M. Stoltz. Tetrahedron 2022, 132940. Part-per-Trillion Trace Selective Gas Detection Using Frequency Locked Whispering-Gallery Mode Microtoroids. Cheng Li, Trevor Lohrey, Phuong-Diem Nguyen, Zhouyang Min, Yisha Tang, Chang Ge, Zachary P. Sercel, Euan McLeod, Brian M. Stoltz, Judith Su. ACS Appl. Mater. Interfaces 2022, 14, 42430–42440. Ir-Catalyzed Asymmetric Allylic Alkylation of Dialkyl Malonates Enabling the Construction of Enantioenriched All-Carbon Quaternary Centers. Farbod A. Moghadam,* Elliot F. Hicks,* Zachary P Sercel, Alexander Q. Cusumano, Michael D. Bartberger, Brian M. Stoltz. J. Am. Chem. Soc. 2022, 144, 7983–7987 Iridium-Catalyzed Asymmetric trans-Selective Hydrogenation of 1,3-Disubstituted Isoquinolines. Alexia N. Kim, Aurapat Ngamnithiporn, Michael D. Bartberger, Brian M. Stoltz. Chem. Sci. 2022, 13, 3227-3232. Isotope effects at the origin of life: Fingerprints of the Strecker synthesis. L. Chimiak, J. Eiler, A. Sessions, C. Blumenfeld, M. Klatte, Brian M. Stoltz. Geochimica et Cosmochimica Acta 2022, 321, 78–98. Some Unusual Transformations of a Highly Reactive α-Bromocaranone. Adrian E. Samkian, Zachary P. Sercel, Scott C. Virgil, Brian M. Stoltz. Tetrahedron Lett. 2022, 89, 153496.