The Krische Research Group - NATURAL PRODUCT SYNTHESIS

Natural Product Synthesis

“Formal Synthesis of Fostriecin via Asymmetric Alcohol-Mediated Carbonyl Allylation,” Pfaffinger, D. E.; Krische, M. J. Org. Lett. 2025, 27, DOI: 10.1021/acs.orglett.5c01026.

“Catalytic Enantioselective C-C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents,” Wu, J.; Verboom, K. L.; Krische, M. J. Chem. Rev. 2025, 105, 13715. (DOI: 10.1021/acs.chemrev.4c00858.)

“Total Synthesis and Structural Revision of the Phenylnaphthacenoid Type II Polyketide Antibiotic Formicamycin H via Ruthenium-Catalyzed Hydrogen Auto-Transfer [4+2] Cycloaddition,” Hu, G.; Doerksen, R. S.; Ambler, B. R.; Krische, M. J. J. Am. Chem. Soc. 2024, 146, 26351. (DOI: org/10.1021/jacs.4c09068.)

“β-Hydroxy Propionates as Malonic Semialdehyde Proelectrophiles in Enantioselective Butadiene-Mediated Crotylation: Total Synthesis of Octalactins A and B,” Wu, J.; Krische, M. J. Org. Lett. 2024, 26, 4830. (DOI: 10.1021/acs.orglett.4c01644.)

“Synthesis of the C30-C41 Side Chain of (Proposed) Neaumycin B: A Contiguous Stereohextet,” Lee, D. S.; Maejima, S.; Krische, M. J. Org. Lett. 2023, 25, 6763.

“Enantioselective Transfer Hydrogenative Cycloaddition Unlocks the Total Synthesis of SF2446 B3: Aglycone of the Arenimycin and SF2446 Type II Polyketide Antibiotics,” Huynh, N. O.; Hodík, T.; Krische, M. J. J. Am. Chem. Soc. 2023, 145, 17461 (DOI: 10.1021/jacs.3c06225).

“Allyl Alcohol as an Acrolein Equivalent in Enantioselective C-C Coupling: Total Synthesis of Amphidinolides R, J, and S,” Meyer, C. C.; Verboom, K. L.; Evarts, M. M.; Jung, W.-O.; Krische, M. J. J. Am. Chem. Soc 2023, 145, 8242 (DOI: 10.1021/jacs.3c01809).

“Ruthenium-Catalyzed Butadiene-Mediated Crotylation and Oxazaborolidine-Catalyzed Vinylogous Mukaiyama Aldol Reaction for the Synthesis of C1-C19 and C23-C35 of Neaumycin B,” Liang, X.; Yoo, M.; Schempp, T. Maejima, S.; Krische, M. J. Angew. Chem. Int. Ed. 2022, 61, e202214786.

“Total Synthesis of The Acetyl CoA Carboxylase Inhibitor Soraphen A: Asymmetric Tsuji Reduction Enables Successive Olefin Metathesis,” Schempp, T. T.; Krische, M. J. J. Am. Chem. Soc. 2022, 144, 2, 1016-1022.

“Total Synthesis of Leiodermatolide A via Transfer Hydrogenative Allylation, Crotylation and Propargylation: Polyketide Construction beyond Discrete Allyl- or Allenylmetal Reagents,” Siu, Y.-M.; Roane, J.; Krische, M. J. J. Am. Chem. Soc. 2021, 143, 10590.

“Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol-Mediated syn- and anti-Diastereoselective Carbonyl Crotylation,” Yoo, M.; Krische, M. J. Angew. Chem. Int. Ed. 2021, 60, 13921.

"Enantioselective Total Synthesis of Andrographolide and 14-Hydroxy-Colladonin: Carbonyl Reductive Coupling and trans-Decalin Formation via Hydrogen Transfer," Yang, L.; Wurm, T.; Poudel, B. S.; Krische, M. J. Angew. Chem. Int. Ed. 2020, 59, 23369.

"Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis," Doerksen, R. S.; Meyer, C. C.; Krische, M. J. Angew. Chem. Int. Ed. 2019, 58, 14055.

“Total Synthesis and Structural Validation of Phosdiecin A via Asymmetric Alcohol-Mediated Carbonyl Reductive Coupling,” Della-Felice, F.; Sarotti, A. M.; Krische, M. J. Pilli, R. J. Am. Chem. Soc. 2019, 141, 13778.

“Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction,” Cabrera, J. M.; Krische, M. J. Angew. Chem. Int. Ed. 2019, 58, 10718.

“Enantioselective Ruthenium Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction,” Turnbull, B. W. H.; Ambler, B. R.; Suravarapu, S. R.; Huynh, N. O.; Krische, M. J. J. Am. Chem. Soc. 2018, 140, 9091.

“Ru-Catalyzed Insertion of Adjacent Diol Carbon Atoms into C-C bonds: Entry to Type II Polyketides,” Bender, M.; Turnbull, B. W. H.; Ambler, B. R.; Krische, M. J. Science 2017, 357, 779.

"Synthesis of the C(1)-C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C-C Bond Formation," Roane, J.; Wippich, J.; Ramgren, S. D.; Krische, M. J. Org. Lett. 2017, 19, 6634.

http://pubs.acs.org/doi/pdf/10.1021/acs.orglett.7b03351

"Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation," Shin, I.; Hong, S.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 14246.

http://pubs.acs.org/doi/pdf/10.1021/jacs.6b10645

"Evaluation of Chromane-Based Bryostatin Analogues Prepared via Hydrogen-Mediated C-C Bond Formation: Potency Does Not Confer Bryostatin-Like Biology," Ketcham, J. M.; Volchkov, I.; Chen, T.-Y.; Blumberg, P. M.; Kedei, N.; Lewin, N. E.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 13415.

http://pubs.acs.org/doi/pdf/10.1021/jacs.6b08695

"Total Synthesis of Oridamycin A, Triptoquinone B and C and Isoiresin via Catalytic Enantioselective Formation of All-Carbon Quaternary Centers: Modular Terpenoid Construction," Feng, J.; Noack, F.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 12364.

http://pubs.acs.org/doi/pdf/10.1021/jacs.6b08902

"Total Synthesis of (+)-SCH 351448 via Transfer Hydrogenative C-C Coupling: Efficiency via Chemoselectivity and Redox-Economy Powered by Metal Catalysis," Wang, G.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 8088.

http://pubs.acs.org/doi/pdf/10.1021/jacs.6b04917

"Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis," Feng, J.; Kasun, Z. A.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 5467 (Perspective Article).

http://pubs.acs.org/doi/pdf/10.1021/jacs.6b02019

"Total Synthesis of Cryptocaryol A via Enantioselective Iridium Catalyzed Alcohol C-H Allylation," Perez, F.; Waldeck, A. R.; Krische, M. J. Angew. Chem. Int. Ed. 2016, 55, 5049.

http://onlinelibrary.wiley.com/doi/10.1002/anie.201600591/abstract;jsessionid=1C84F1CA9136A00E4EBB5DBB7E03795D.f04t01

"Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols," Shin, I.; Krische, M. J. Org. Lett. 2015, 17, 4686.

http://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5b02056

"Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester," Kasun, Z. A.; Gao, X.; Lipinski, R. M.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 8900.

http://pubs.acs.org/doi/pdf/10.1021/jacs.5b05296

“Synthesis of seco-B-Ring Bryostatin Analogue WN-1 via C-C Bond Forming Hydrogenation: Critical Contribution of the B-Ring in Determining Bryostatin- and PMA-Like Properties,” Andrews, Ian P.; Ketcham, J. M.; Blumberg, P. M.; Kedei, N.; Lewin, N. E.; Krische, M. J. J. Am. Chem. Soc. 2014, 136, 13209.

http://pubs.acs.org/doi/pdf/10.1021/ja507825s

“Polyketide Construction via Hydrohydroxyalkylation and Related Alcohol CH Functionalizations: Reinventing the Chemistry of Carbonyl Addition,” Dechert-Schmitt, A.-M. R.; Schmitt, D. C.; Gao, X.; Itoh, T.; Krische, M. J. Nat. Prod. Rep. 2014, 31, 504.

http://pubs.rsc.org/en/content/articlelanding/2014/np/c3np70076c

“Asymmetric Alcohol C-H Allylation and syn-Crotylation: C9-C20 of Tetrafibricin,” Itoh, T.; Montgomery, T. P.; Recio, A., III; Krische, M. J. Org. Lett. 2014, 16, 820.

http://pubs.acs.org/doi/pdf/10.1021/ol403566w

“Total Synthesis of (+)-Trienomycins A and F via C-C Bond-Forming Hydrogenation and Transfer Hydrogenation,” Del Valle, D. J.; Krische, M. J. J. Am. Chem. Soc. 2013, 135, 10986.

http://pubs.acs.org/doi/pdf/10.1021/ja4061273

“Total Synthesis of Cyanolide A in the Absence of Protecting Groups, Chiral Auxiliaries or Premetallated Carbon Nucleophiles,” Waldeck, A. R.; Krische, M. J. Angew. Chem. Int. Ed.2013, 52, 4470.

“Total Synthesis of 6-Deoxyerythronolide B via C-C Bond-Forming Transfer Hydrogenation,” Gao, X.; Woo, S. K.; Krische, M. J. J. Am. Chem. Soc. 2013, 135, 4223.

http://pubs.acs.org/doi/pdf/10.1021/ja4008722

“Total Synthesis of Bryostatin 7 via C-C Bond Forming Hydrogenation: Merged Redox-Construction Events for Synthetic Efficiency,” Lu, Y.; Woo, S. K.; Krische, M. J. J. Am. Chem. Soc.2011, 133, 13876.

http://pubs.acs.org/doi/pdf/10.1021/ja205673e

“C(21)-C(40) of Tetrafibricin via Metal Catalysis: Beyond Stoichiometric Chiral Reagents, Auxiliaries and Premetallated Nucleophiles,” Kumpulainen, E. T. T.; Kang, B.; Krische, M. J. Org. Lett. 2011, 13, 2484.

http://pubs.acs.org/doi/pdf/10.1021/ol200735r

“Total Synthesis of (+)-Roxaticin via C-C Bond Forming Transfer Hydrogenation: A Departure from Stoichiometric Chiral Reagents, Auxiliaries and Premetallated Nucleophiles in Polyketide Construction,” Han, S. B.; Hassan, A.; Kim, I. S.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 15559.

http://pubs.acs.org/doi/abs/10.1021/ja1082798

“Synthesis of the Cytotrienin A Core via Metal Catalyzed C-C Coupling,” Rossle, M.; Del Valle, D. J.; Krische, M. J. Org. Lett. 2011, 13, 1482.

http://pubs.acs.org/doi/pdf/10.1021/ol200160p

“Concise Synthesis of the Bryostatin A-Ring via Consecutive C-C Bond Forming Transfer Hydrogenations,” Lu, Y.; Krische, M. J. Org. Lett. 2009, 11, 3108.

http://pubs.acs.org/doi/pdf/10.1021/ol901096d

"Asymmetric Total Synthesis of the Iridoid -Glucoside (+)-Geniposide via Phosphine Organocatalysis." Jones, R. A.; Krische, M. J. Org. Lett. 2009, 11, 1849.

http://pubs.acs.org/doi/pdf/10.1021/ol900360h

“Enantioselective Reductive Coupling of Alkynes and -Ketoaldehydes via Rhodium-Catalyzed Hydrogenation: An Approach to Bryostatin Substructures,” Cho, C.-W.; Krische, M. J. Org. Lett. 2006, 8, 891.

http://pubs.acs.org/doi/pdf/10.1021/ol052976s

“Intramolecular Organocatalytic [3+2] Dipolar Cycloaddition: Stereospecific Cycloaddition and The Total Synthesis of (±)-Hirsutene,” Wang, J.-C.; Krische, M. J. Angew. Chem. Int. Ed.2003, 42, 5855.

“Catalytic Crossed Michael Cycloisomerization of Thioenoates: Total Synthesis of ()-Ricciocarpin A,” Agapiou, K.; Krische, M. J. Org. Lett. 2003, 5, 1737.

http://pubs.acs.org/doi/pdf/10.1021/ol030035e

Report abuse