Thomas R. Hoye Jacob T. Edwards 7/1/17 Research Interests Total - PowerPoint PPT Presentation

Baran Group Meeting Thomas R. Hoye Jacob T. Edwards 7/1/17 Research Interests Total synthesis of complex natural products, organometallic chemistry, olefin metathesis (RRCM), stereochemistry determination via NMR, No-D NMR spectroscopy, polymer synthesis, natural product structure determination, hexadehydro-Diels- Thomas R. Hoye Alder reaction, and more Education Career Snapshot B.S. Bucknell University, 1972 - > 200 publications M.S. Bucknell University, 1972 (Harold W. Heine) - 14 patents Ph.D. Harvard University, 1976 (Robert B. Woodward) - > 150 undergraduates, 14 masters students, 81 Ph.D. students, and > 40 postdocs - Trimethyl Phosphonoacetate (EROS Article) Professional Career - Academic offspring include Bongjin Moon (Sogang University, Seoul, South Korea), Paul R. Assistant Professor, University of Minnesota, 1976 Hanson (University of Kansas), Mark J. Kurth (UC-Davis), Christopher S. Jeffrey (University of Professor, University of Minnesota, 1988 Nevada, Reno), Dawen Niu (Sichuan University) - Collaborators include P. Sorensen (UMN Department of Fisheries), M. Hillmyer (UMN Awards and Honors Department of Chemistry), C. Macoscko (UMN Department of Chemical Engineering and Alfred P. Sloan Foundation Research Fellowship, 1985 Materials Science), K. Mayo (UMN College of Biological Sciences) Award for Outstanding Contributions to Post-baccalaureate, Graduate, and Professional Education, 1999 Academy of Distinguished Teachers, University of Minnesota, 1999 Top Six Most Cited Works: Merck Professor of Chemistry, University of Minnesota, 2002–2007, 2009–2014 Determination of absolute configuration of stereogenic carbinol centers in annonaceous Morse-Alumni Award for Excellence in Undergraduate Teaching, University of Minnesota, 2007 cetogenins by proton and fluorine 19-NMR analysis of Mosher ester derivatives, J. Am. Chem Minnesota Award for Outstanding Contributions to the Chemical Sciences, ACS Minnesota Soc. 1992 , 114 , 10203 (263 citations) Section, 2014 Ernest Guenther Award in the Chemistry of Natural Products, American Chemical Society, Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) 2015 carbinol carbons, Nature Protocols 2007 , 2 , 2451 (242 citations) Royal Society of Chemistry Robert Robinson Award, 2016 Arthur C. Cope Scholar Award, American Chemical Society, 2017 Some allylic substituent effects in ring-closing metathesis reactions: Allylic alcohol activation, College of Science and Engineering Distinguished Professor, University of Minnesota Org. Lett. 1999 , 1 , 1123 (167 citations) Mixture of new sulfated steroids functions as a migratory pheromone in the sea lamprey, Nat. Chem. Biol. 2005 , 1 , 324 (153 citations) The hexadehydro-Diels-Alder reaction, Nature , 2012 , 490 , 208 (149 citations) Relay ring-closing meathesis (RRCM): A strategy for directing metal movement throughout olefin metathesis sequences, J. Am. Chem. Soc. 2004 , 126 , 10210 (141 citations)

Baran Group Meeting Thomas R. Hoye Jacob T. Edwards 7/1/17 OH Me Targets Completed by the Hoye Group H O Me OH NH Me O O Me OH Me OH Me O Me OMe HO Me Br O Br Me NH NH H Me Me Me Me OH OMe (±)-3 β -bromo-8-epicaparrapi oxide (±)-aplysistatin (±)-megaphone (formal) HO Me HO Me J. Org. Chem. 1979 , 44 , 3461 J. Am. Chem. Soc. Tet. Lett. 1983 , 24 , 4769 Me Me 1979 , 101 , 5065 OMe OH J. Am. Chem. Soc. 1982 , 104 , 6704 Me Me OH O N O OMe OR OMe OH 9 HN Me HO O korupensamine A korupensamine B H J. Org. Chem. 1999 , 64 , 7184 J. Org. Chem. 1999 , 64 , 7184 Me OH michellamines A–C O Tet. Lett. 1994 , 35 , 8747 (+)-(15,16,19,20,23,24)-hexepi-uvaricin J. Am. Chem. Soc. 1991 , 113 , 9369 O H OH Me OH Me Me OMe O Me NH N HN N Me AcO (+)-xestospongin A HO Me HO Me Me OH J. Am. Chem. Soc. 1994 , 116 , 2617 Me Me Me (–)-xestospongin C (C9 epimer) O J. Am. Chem. Soc. 1996 , 118 , 12074 O OH Me HO OMe OMe OMe OH OMe OMe korupensamine C ( ent )-korupensamine D ancistrobrevine B Me O Tet. Lett. 1996 , 37 , 3097 O Tet. Lett. 1996 , 37 , 3097 Tet. Lett. 1996 , 37 , 3099 H O (–)-bullatacin Me korupensamine D O Tet. Lett. 1993 , 34 , 5043 J. Org. Chem. 1999 , 64 , 7184 (+)-bullatacin (shown above) H O Tet. Lett. 1995 , 36 , 1981 O O OH (±)-carabrone (formal) Me J. Org. Chem. 1995 , 60 , 4184 HO Me Me HO O OH O Me (+)-asamicin HO OH Me O Me H Tet. Lett. 1995 , 36 , 1981 O H O O HO OH O O CO 2 Me H Me Me Me Me HO O O HO Me (±)-ancistrofuran (±)-differolide (±)-sarracenin J. Org. Chem. 1981 , 46 , 1198 (–)-cylindocyclophane A Org. Lett. 1999 , 1 , 277 J. Org. Chem. 1989 , 54 , 688 J. Am. Chem. Soc. 2000 , 122 , 4982

Baran Group Meeting Thomas R. Hoye Jacob T. Edwards 7/1/17 O Targets Completed by the Hoye Group Me O O O Me O Me Me H O OH NH O HO O O O O O O N Me Me Me Me OH H O O Me Me Me Me NH N Me O O O HO Me (+)-scyphostatin (core) O NH Et Org. Lett. 2010 , 12 , 52 H OH O MeO O O O O (–)-dactylolide (± )-leuconolam zampanolide Me J. Am. Chem. Soc. Chem. Sci. 2013 , 9 , 589 J. Am. Chem. Soc. Cl 2003 , 125 , 9576 2003 , 125 , 9576 O (–)-callipeltoside A C 12 H 25 Me Me J. Org. Chem. 2010 , 75 , 7052 O OH H H O C 12 H 25 H OH O O O Me Me (± )-paracaseolide A H MeO Cl O HO Nature Chemistry 2015 , 7 , 641 OMe Me Useful Resources H CO 2 H O H OH O A practical guide to first-order multiplet analysis in 1H NMR spectroscopy. O J. Org. Chem. 1994 , 59 , 4096. O O OH Me O N Me H Me A method for easily determining coupling constant ( J ) values OAc J. Org. Chem. 2002 , 67 , 4014 OH HO (± )-UCS1025A (–)-haterumalide NA/(–)-oocydin A OMe MTPA (Mosher) amides of cyclic secondary amines: Conformational aspects and a useful J. Am. Chem. Soc. J. Am. Chem. Soc. (+)-peloruside A method for assignment of amine configuration. 2005 , 127 , 6950 2006 , 128 , 2551 Angew. Chem. Int. Ed. J. Org. Chem. 1996 , 61 , 2056. O 2010 , 49 , 6151 A convenient synthesis of dimethyl(diazomethyl)phosphonate (Seyferth/Gilbert reagent). OH O O OH J. Org. Chem. 1996 , 61 , 2540. HO O C 12 H 25 No-D NMR (no deuterium proton NMR) spectroscopy: A simple yet powerful method for Me (+)-gigantecin analyzing reaction and reagent solutions. Org. Lett. 2004 , 6 , 953 Org. Lett. 2006 , 8 , 3383 OH O O No-D NMR spectroscopy as a convenient method for titering organolithium (RLi), RMgX, and Me Me Me LDA solutions. Org. Lett. 2004 , 6 , 2567. O O Me Me Reaction titration: A convenient method for titering reactive hydride agents (Red-Al, LiAlH4, OH Me O N DIBALH, L-Selectride, NaH, and KH) by No-D NMR Spectroscopy. Org. Lett. 2005 , 7 , 2205. Me H Me N Me H Me Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons. Nature Protocols 2007 , 2 , 2451 (± )-mahanimbine koenidine (–)-okilactomycin D J. Am. Chem. Soc. A guide to small-molecule structure assignment through computation of (1H and 13C) NMR J. Am. Chem. Soc. Org. Lett. 2012 , 14 , 828 chemical shifts. Nature Protocols 2014 , 9 , 643 2016 , 138 , 13870 2016 , 138 , 13870 R. B. Woodward lectures: http://www1.chem.umn.edu/groups/hoye/links/index.php