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Steven Ley 03/10 2012 Baran Group Meeting Lars Jørgensen Steven Ley 03/10 2012 Biography Major Prizes and Awards Born December 10, 1945 in Stamford, 1980 Corday Morgan Medal and Prize (Royal Society of Chemistry) Lincolnshire, England. 1981 The 1981-1983 Hickinbottom Research Fellowship (joint 1st recipient) (RSC) 1983 Pfizer Academic Award (1st recipient) (Pfizer PLC) Education 1988 Tilden Lectureship and Medal (Royal Society of Chemistry) 1969 BSc (first class hons) from 1989 Award for Organic Synthesis (Royal Society of Chemistry) Loughbourough University. 1992 Pedler Lectureship, Medal and Prize (Royal Society of Chemistry) 1969-1972 PhD from Loughbourough 1993 Simonsen Lectureship and Medal (Royal Society of Chemistry) University (Prof. H. Heaney). 1993 Award for Natural Product Chemistry (Royal Society of Chemistry) 1972-74 Postdoc at Ohio State University 1994 Adolf Windaus Medal (German Chemical Society - Georg-August University) (Prof. Leo. A. Paquette) 1995 The Novartis Research Fellowship (1995 - 2007) (Novartis) 1995 The Flintoff Medal (Royal Society of Chemistry) 1974-75 Postdoc at Imperial College (Prof. Sir 1996 The Dr. Paul Janssen Prize for Creativity in Organic Synthesis (Janssen R. F.) Derek H.R. Barton) 1996 George Kenner Prize and Lectureship (University of Liverpool) 1997 The Bakerian Lecturer (The Royal Society) 1998 The Rhône-Poulenc Lectureship, Medal and Prize (Royal Society of Chemistry) Academic Career 1999 The GlaxoWellcome Award for Outstanding Achievement in Organic Chemistry 1976-83 Lecturer, Imperial College (1st recipient) 1983-92 Prof. of Organic Chemistry, Imperial College 2000 The Davy Medal (The Royal Society) 1989-92 Head of Department, Imperial College 2001 Haworth Memorial Lectureship, Medal and Prize (Royal Society of Chemistry) 1992-present BP (1702) Prof. of Organic Chemistry, Cambridge University 2001 August-Wilhelm-von Hofmann Medal (Gesellschaft Deutscher Chemiker) 1992-present Head of Organic Chemistry, Cambridge University 2001 The Pfizer Award for Innovative Science (1st chemist recipient) 1993-present Fellow of Trinity College, Cambridge University 2003 The Ernest Guenther Award in the Chemistry of Natural Products (American Chemical Society) 2003 Royal Society Wolfson Merit Award Research Interests 2003 Industrially-Sponsored Award in Carbohydrate Chemistry (The Royal Society of Natural products Chemistry) Medicinal chemistry 2004 The Messel Medal Lecture (The Society of Chemical Industry) Asymmetric organocatalysis 2006 The Robert Robinson Lectureship, Medal and Prize (The Royal Society of Solid-supported reagents Chemistry) Microwave chemistry 2006 The Nagoya Gold Medal (Banyu Life Science Foundation International, Japan) Flow chemistry 2007 Award for Creative Work in Synthetic Organic Chemistry (ACS) 2008 High Throughput Drug Discovery Methodologies Award (The Royal Society of Methodology Chemistry) - Ley's TPAP reagent 2009 Heinrich Wieland Prize awarded for outstanding achievements in the synthesis of - -allyl tricarbonyliron complexes key natural products (Boehringer Ingelheim) - 1,2-diacetals and dispiroketals 2009 Tetrahedron Prize for Creativity in Organic Chemistry 2010 Paracelsus Prize (Swiss Chemical Society) 2011 Royal Medal (Royal Society) Baran Group Meeting Lars Jørgensen Steven Ley 03/10 2012 Early Years Post Doc with Prof. Leo Paquette (12 papers) PhD with Prof. Harry Heaney (17 papers) Synthesis of (-)-Triquinacene-2-carboxylic Acid NC Benzyne cycloaddition and their rearrangements I K2CO3 conc. HCl NMe2 NC I2, Pb(OAc)4 THF/H2O NC reflux 250W then MeO if CN 82% O O tungsten lamp O O CH N R=H 2 2 O OH F F 56% 68% R R F F EtOH/H2O O heat 1. Burgess reagent, 56% F NMe F NMe 2 2 Me 2. KOH, EtOH, ~quant. F F if R=Me HO J. Chem. Soc., Chem. Commun. 1970, 1184 O (-)-Triquinacene-2-carboxylic acid Me Me Me F O F F F Me J. Am. Chem. Soc., 1974, 96, 312 F Me F Me F F H+ F Me F OMe F OMe F OMe F F F F NC CN Fe(CO) + 3 H NC CN NC NC CAN NC NC NC NC R OH Fe(CO)3 CN O CN F Me F F O O Me OH Me F F F J. Am. Chem. Soc., 1975, 97, 7273 O F Me F Me F Me F F H+ F Alkali Metal Reduction Studies of cis- and trans-Bicyclo[6.1.0]nona-2,4,6-trienes in J. Chem.Soc., Perkin Trans. 1, 1974, 2711 Liquid Ammonia N9Alkylation of indoles H Me H Me Me 2e- H = R-I or BnBr N N KOH H Me H Me DMSO R H H J. Chem. Soc., Perkin Trans. 1, 1973, 499 2e- = Org. Synth., 1974, 54, 58 Me J. Am. Chem. Soc., 1974, 96, 6670 Baran Group Meeting Lars Jørgensen Steven Ley 03/10 2012 Post doc work and other publication with Prof. Barton (28 papers) Removal of 1,3 -Dithiolan Protecting Groups by Benzeneseleninic Anhydride Initial project: The Stability of N,N-Dialkylthiohydroxylamines O O Se Se R S Ph O Ph R X O Li/NH S R S R S 3 N S X X J. Chem. Soc., Chem. Commun., 1977, 751-752 J. Chem. Soc., Chem. Commun., 1975, 855 Oxidation of Phenols to ortho-Quinones using Diphenylseleninic Anhydride Dehydrogenation of steroidal ketones using benzeneseleninic anhydride OH O O O O O O O Se Se Ph O Ph Se Se Se Ph O Ph Ph syn-elimination 1976 O O O J. Chem. Soc., Chem. Commun., , 985 H H H Regeneration of Ketones from Hydrazones, Oximes, and Semicarbazones by Benzeneseleninic Anhydride In contrast to selenium dioxide, is relatively unreactive towards olefins O O J. Chem. Soc., Chem. Commun., 1978, 130-131 R R H Se Se N Ph O Ph Ar N R O R mechanism? THF parent ketone Conversion of Thiocarbonyl Compounds into Their Corresponding Oxo Derivatives O O Se Se S Ph O Ph O 1977 R R' R R' J. Chem. Soc., Chem. Commun., , 445 X Y X Y xanthates, thioesters, thiocarbonates, Oxidation of Aldehyde Hydrazones, Hydrazo Compounds, and Hydroxylamines thioamides, and thiones J. Chem. Soc., Chem. Commun., 1978 with Benzeneseleninic Anhydride , 393-394 O O O Oxidation of Alcohols using Benzeneseleninic Anhydride H Se Se H H Ph O Ph N N Ar N R Ar N R O O THF H OH Se Se O acylazo-derivatives Ph O Ph R R' R R' J. Chem. Soc., Chem. Commun., 1978, 276-277 J. Chem. Soc., Chem. Commun., 1978, 952-954 Preparation of Aldehydes and Ketones by Oxidation of Benzylic Hydrocarbons with Benzeneselenininic Anhydride O O O Se Se Ph O Ph Ar R Ar R Tetrahedron Lett., 1979, 3331 Baran Group Meeting Lars Jørgensen Steven Ley 03/10 2012 Entering the Field of Natural Product Synthesis Selenium mediated C-C bond forming cyclization - drimane sesquiterpenes O N SePh H H CO2Me O O CO2Me CO2Me ZnI2 CO2Me Pd/C, H2 CO2Me O E E MeO2C HCl (trace) O O E = CO2Me PhSe 110 C MeOH H H 95% 80% e lit e cinnamolide /C LiAlH 3 4 O t. C n 90% 2 a J. Chem. Soc., Chem. Commun., 1980, 1028 g u A q ~ J. Chem. Soc., Chem. Commun., 1980, 1173 OAc OAc OH O OH O Tetrahedron Lett., 1981, 2601 OAc SeO2 OAc Ac2O, pyr OH 3 steps 80% ~quant. H H H H Total Synthesis of hirsutene [P P drimenin O h 4 ] 1. K2CO3, MeOH Swern [R u 2. DMSO, TFAA O 95% 3 N SePh SePh O 5 2 C O 45% % l HO C H E HO 3 ] HO 2 O CHO O 2 steps O OHC OH Cunninghamella CHO elegans CHO CO2H SnCl4 H H H 45% H H 90% H HO H H H warburganal daniol polygidial isodrimeninol LDA then LAH 66% J. Chem. Soc., Chem. Commun., 1981, 507 O , 1981, 3909 SePh N SePh OH Tetrahedron Lett. SePh O SePh O J. Chem. Soc., Perkin Trans. 1, 1983, 1579 H H H 1. Raney Ni, 83% O 2. CH Br Zn 2 2, Bu3P H H TiCl4, 97% H H 63% H H hirsutene J. Chem. Soc., Chem. Commun., 1982, 1252 Tetrahedron, 1985, 41, 4765 Baran Group Meeting Lars Jørgensen Steven Ley 03/10 2012 -Allyltricarbonyliron lactone complexes OMe HO O O OMe 1. PtO2, H2 Fe(CO) (OC) Fe O O O 3 3 O 2. DIBALH CO, 240 atm O Fe2(CO)9 3. PhSO2H H H + H O O PhO2S O O O O THF 140 C, PhH H H O -lactone H O O OH O O O OMe H OH HO Fe2(CO)9 Fe(CO) (OC) Fe CO, 240 atm avermectin B1a O O 3 3 O steps O S O O O OH THF + H 140 C, PhH O H acrolein -lactone oleandrose Spiroketals and 2-benzenesulfonyl cyclic ethers J. Chem. Soc., Perkin Trans. 1, 1991, 667-692 R O OR CAN steps (OC) Fe O OH EtOH O OH O O O R 3 O R PhSO2H, ROH, O O PhSO2H, O O MgBr2, Et3N CaCl2 MgBr2 O OH CaCl2 -lactone valilactone N H H PhSO2H OSiR3 Tetrahedron, 1991, 47, 9299 1. BuLi R O R R R 2. RX O SO Ph AlCl O R 2 3 O R RMgBr, ZnBr2 O or Fe(CO)3 1. BuLi 1. BuLi O OH HO OH R O R NaBH(OAc)3 steps 2. I(CH2)4OTHP 2. RX taurospongin A O 3. H+ 3. NaNaphth. O R TBSO OTBS TBSO OTBS spiroketals Org. Biomol. Chem., 2003, 1, 1664 Tetrahedron Lett., 1985, 26, 535 Tetrahedron, 1986, 42, 4333 Tetrahedron, 1989, 45, 4293 Baran Group Meeting Lars Jørgensen Steven Ley 03/10 2012 Dispiroketals and 1,2-Diacetals Just one example: R3 OMe OMe LHMDS 6 O O R O OR O O THF OH 2 3 2 OMe O OMe O O R 4R O 1R then aldehyde O R1 R O R Desymmetrized Glycolic Acid de% > 92+ O OR5 Org.
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