Publications

A selected list of publications corresponding to each research area:

Polycyclic ether natural products:

“Biomimetic Synthesis via Polyepoxide Cyclizations.” Frank E. McDonald, Rongbiao Tong, Jason C. Valentine, and Fernando Bravo, Pure and Applied Chemistry, 2007, 79, 281-291.  link 

PAC 2007 abstract

“Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of Abudinol B, and Reassessment of the Structure of Muzitone.”  Matthew A. Boone, Rongbiao Tong, Frank E. McDonald, Sheri Lense, Rui Cao, and Kenneth I. Hardcastle, Journal of the American Chemical Society, 2010, 132, 5300-5308.  link 

JACS 2010 muzitone abstract

“Synthesis of 15,28-Dideoxy-15,28-didehydrothyrsenol.” Mary A. Smart and Frank E. McDonald, Heterocycles, 2012, 86, 535-553.  link

Het 2012 thyrsenol abstract

“Stereoselectivity of electrophile-promoted oxacyclizations of 1,4-dihydroxy-5-alkenes to 3-hydroxytetrahydropyrans.” Frank E. McDonald, Kento Ishida, and Jessica A. Hurtak. Tetrahedron, 2013, 69, 7746-7758.  link

Tet 2013 abstract

“Iodoetherification of Conformationally Restricted Dienyl Alcohols: Unexpected Formation of Oxocenes by 8-endo-mode Oxacyclizations.”  Kristen L. Stoltz, Andrea-Nekane R. Alba, Frank E. McDonald, Marika B. Wieliczko, and John Bacsa, Heterocycles, 2014, 88, 1519-1526.  link

Het 2014 abstract

“Regioselectivity of mercury-promoted oxacyclizations of alkynyl diols.” Jessica A. Hurtak and Frank E. McDonald, SYNLETT, 2017, 28, 2951-2955. link

“Synthesis of the ABC substructure of brevenal by sequential exo-mode oxacyclizations of acyclic polyene precursors.” Jessica A. Hurtak and Frank E. McDonald, Organic Letters, 2017, 19, 6036-6039.  link

“Stereoselective Synthesis of Pyrans from Epoxyalkenes: Dual Catalysis with Palladium and Brønsted Acid.”  Noah A. Setterholm and Frank E. McDonald, The Journal of Organic Chemistry, 2018, 83, 6259-6274.  link

“Sequential exo-mode oxacyclizations for the synthesis of the CD substructure of brevenal.”  Noah A. Setterholm and Frank E. McDonald, The Journal of Antibiotics2019, DOI: 10.1038/s41429-018-0124-1.  link

Acyclic and macrocyclic natural products:

“Total Synthesis of the Polyene-Polyol Macrolide RK-397, Featuring Cross-Couplings of Alkynylepoxide Modules.”  Svetlana A. Burova and Frank E. McDonald, Journal of the American Chemical Society, 2004, 126, 2495-2500.  link

JACS 2004 RK397 abstract

“Modular Synthesis of the C9-C27 Degradation Product of Aflastatin A via Alkyne-Epoxide Cross-Couplings.”  Omar Robles and Frank E. McDonald, Organic Letters, 2008, 10, 1811-1814.  link

OL 2008 aflastatin abstract

“Total Synthesis of the Sphingolipid Biosynthesis Inhibitor, Fumonisin B1.”  Claney L. Pereira, Yi-Hung Chen, and Frank E. McDonald, Journal of the American Chemical Society, 2009, 131, 6066-6067.  link

JACS 2009 fumonisin abstract

“Convergent Synthesis of Fostriecin via Selective Alkene Couplings and Regioselective Asymmetric Dihydroxylation.”  Omar Robles and Frank E. McDonald, Organic Letters, 2009, 11, 5498-5501.  link

OL 2009 fostriecin abstract

“Fumonisin: A Template for Methodology Development and Drug Discovery.” Frank E. McDonald, Claney L. Pereira, and Yi-Hung Chen, Pure and Applied Chemistry, 2011, 83, 445-459.  link

PAC 2011 fumonisin and enigmol abstract

“Stereo- and Regioselective Synthesis of 2-Amino-3,5-diols via Stereospecific Crotyl Transfer and Regioselective Aminohydroxylation.” Frank E. McDonald and Claney L. Pereira, Synthesis, 2012, 44, 3639-3648.  link

Synth 2012 enigmol graphical abstract

Oligosaccharides:

“Convergent Synthesis of Digitoxin: Stereoselective Synthesis and Glycosylation of the Digoxin Trisaccharide Glycal.”  Frank E. McDonald and K. Subba Reddy, Angewandte Chemie International Edition in English, 2001, 40, 3653 – 3655.  link

ACIE 2001 Reddy abstract

“Fischer carbene catalysis of alkynol cycloisomerization: Application to the synthesis of the altromycin B disaccharide.” BonSuk Koo and Frank E. McDonald, Organic Letters, 2007, 9, 1737-1740.  link

OL 2007 BonSuk abstract

“Stereo- and Regioselective Glycosylations to the Bis-C-arylglycoside of Kidamycin.” ZhongBo Fei and Frank E. McDonald, Organic Letters, 2007, 9, 3547-3550.  link

OL 2007 ZhongBo abstract

“1,5-α-D-Mannoseptanosides, Ring-size Isomers That Are Impervious to α-Mannosidase-catalyzed Hydrolysis.”  Matthew A. Boone, Frank E. McDonald, Joseph Lichter, Stefan Lutz, Rui Cao, and Kenneth I. Hardcastle, Organic Letters, 2009, 11, 851-854.  link

OL 2009 septanoside abstract

“Brønsted Acid-Promoted Glycosylations of Disaccharide Glycal Substructures of the Saccharomicins.” Bradley R. Balthaser and Frank E. McDonald, Organic Letters, 2009, 11, 4850-4853.  link

OL 2009 Balthaser abstract

“Synthesis of Human Milk Oligosaccharides: 2′- and 3-Fucosyllactose.” Claney L. Pereira and Frank E. McDonald, Heterocycles, 2012, 84, 637-655.  linkHMO graphical abstract

Medicinal chemistry:

“Blockade of Glioma Proliferation Through Allosteric Inhibition of JAK2.” Kunyan He, Qi Qi, Chi-Bun Chan, Ge Xiao, Carol Tucker-Burden, Liya Wang, Hui Mao, Hui Tao, Shi-Yong Sun, Xiang Lu, Frank E. McDonald, Hongbo Luo, Qi-wen Fan, William A. Weiss, Daniel J. Brat, and Keqiang Ye, Science Signaling, 2013, 6, ra55   link

“Gram-scale, chemoselective synthesis of N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-2-oxopiperidine-3-carboxamide (HIOC).”  Noah A. Setterholm, Frank E. McDonald, Jeffrey H. Boatright, and P. Michael Iuvone, Tetrahedron Letters, 201556, 3413-3415.  link