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Organic Chemistry from the Eastern Bloc Florina Voica

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Organic Chemistry from the Eastern Bloc Florina Voica Baran Lab GM 08/13/2011 Organic Chemistry from the Eastern Bloc Florina Voica The goal of this presentation is to offer a detailed perspective on the state of art in organic chemistry research in the major academic centers in former Eastern Bloc countries (Poland, Czech Republic, Slovakia, Hungary, Slovenia, Croatia, Serbia, Macedonia, Albania, Bulgaria, Romania, Moldova, Ukraine, Belarus, Lithuania, Latvia, Estonia). The analysis for each individual country consists in identifying the researchers who have made significant contributions to the field. Historic context: - The Eastern Bloc refers to the region in Europe which entered under Soviet influence after WWII (Yalta conferene, 1945); - These were communist countries, either directly reporting to Moscow, or having more "independent" communist regimes; - Under the strict, totalitarian policies, the economic development was "extensive rather than intensive", with chracteristic shortages of goods and minimal innovation; - After the fall of USSR (1989-1991), these countries adopted the free market economic model (and democratic governments), but in most cases the '90s remain a period of slow development (transition period/lost generation); - Nov 1993, The Maastricht Treaty established The European Union; - WIth the exception of Albania, Serbia, Montenegro, Croatia and Russia, all former communist countries are now part of the EU; General aspects: The scientist in society: During the almost half a century of soviet cultural influence, science and technology served an important part of national politics and identity. However, significant efforts were focused on pure science and theoretical research, with little practical applications or economic impact. The educational system "In spite of all the apparent shortcomings and faults, the Russian secondary schools seem to prepare the students relatively well for life and for higher education, especially in the sciences and mathematics. The intensity of the work and the student's motivation to succeed is a big factor. Admission to higher education is a crucial, life-long decision and it is made while the student in still in the secondary school." "In general, the Soviet Educators in higher educational institutions receive and work with a better motivated and selected student than their American counterparts. However, the rigid requirements and screenings have an already built-in weakness due to over-specialization." "The earned Doctor degree is supposed to be based on research work containing a theoretical utilization and the solution of a major scientific problem representing a considerable contribution to science and to practical work. It should have a serious impact". "The earned Doctor degree is not a degree in the American sense, but a sign of recongition which could be compared to our post-doctoral experience. Too many Russians remain in one place to work and study under the same man in one field. This creates inbreeding and an educational system that lacks imagination and produces research contributions not up to the level of effort exerted and manpower used" Chemistry Nobel Prize winners J. Chem. Educ. 1971, 48, 60; 1973, 50, 520. - awarded from 1945-2011; chemists who were residents in their countries of birth when they received the award: Nikolay Semyonov (Russia), 1956 - for work on the mechanism of chain reactions; Jaroslav Heyrousky (Czech Republic), 1959 - for developing the polarographic method of analysis; Vladimir Prelog (Croatia), 1975 - for research into the stereochemistry of molecules and reactions; - awarded from 1945-2011; eastern european born chemists who led their research in other countries: Ilya Prigogine (born Russia), 1977 - for his work on dissipative structures, complex systems, and irreversibility; Roald Hoffmann (born Ukraine), 1981 - for the Woodward-Hoffman rule; Aaron Klug (born Lithuania), 1982 - for his development of crystallographic electron microscopy and his structural elucidation of biologically important nucleic acid-protein complexes George Olah (born Hungary), 1994 - for work on carbocations generated with superacids; Avram Hershko (born Hungary), 2004 - for the discovery of ubiquitin-mediated protein degradation. The pharmaceutical industry: - generic drugs account for more than half of the total market (in value) and almost 3/4 in volume (july 2011); - major generic companies: KrKa (Slovenia), Gedeon Richter (Hungary), PolPharma (Poland), Zentiva (Romania), Pharmstandard (Russia). - highest sales in cardiovascular market, followed by alimentary canal and metabolic disorders; http://blog.pharmexec.com/2009/09/02/pharma-industry-booming-in-eastern-europe/ - importantly, the health care system is run by the government, so obviously there is little impetus for significant R&D programs. http://www.espicom.com/prodcat2.nsf/Product_ID_Lookup/00000396?OpenDocument https://www.mckinseyquarterly.com/Pharmas_generics_opportunity_in_Central_and_Eastern_Europe_2186# Baran Lab GM 08/13/2011 Organic Chemistry from the Eastern Bloc Florina Voica Major Research Centers: O Institute of Organic Chemistry, Polish Academy of Sciences nBuLi, TMS Univ of Warsaw SO2Ph OH Adam Mickiewiecz Univ, Poznan then HClO4, MeOH Warsaw Univ of Technology Gdansk Technical Univ (+)DET, Ti(OiPr)4, TBHP Founding fathers: 1. TsCl, pyr Osman Achmatowicz (1899-1988) - alkaloids isolation 2. (nC9H19)2CuLi (O. Achmatowicz Jr - sugar chemistry, name rxn) Jerzy Suszko (1889-1972) - polycyclic aromatics C9H19 OH Edwin Plazek - heterocyclic chemistry O O Henryk Kuczynski (1909-1991) - terpene chemistry (+)-disparlure Tet. Lett. 1989, 30, 2845 Prof. Jerzy Wicha O O Me Me - born on February 14, 1936, Warsaw, Poland; O - education: Me Me 1. NaOMe, 40% Me H M. Sc.: Moscow State University, 1958 2. H2, Pd/SrSO3 Ph. D.: The University of Warsaw, 1964 OH D. Sc.: The University of Warsaw, 1970 O - positions: O O O 1958-1960 Research Associate, Institute of Pharmaceutical Industry, Warsaw 1960 -1970 Instructor - reader, the University of Warsaw H2, Pd/C 1970 - 1978 Docent, Institute of Organic Chemistry, Polish Academy of Sciences I I Me O 1978 - Professor, the same Institute Me Me - 184 publications (Scifinder) 1. L-selectride Me H - major research topics: steroid synthesis, some guanacastepene, Me H Me H 2. N2H4 prostaglandins research, some methods based on the Julia olefination N2H2 3. I2 reaction. OH OH OH HO HO O H H H SO2Ph TMS OSitBuPh TMS 2 1. tBuNC, NaCNBH nBuLi OSitBuPh2 3 Bu SnCl, AIBN O then MsCl dr 3:1 3 H 2. DHP PhO2S OMs O 86% (over 2 steps) 3. MeLi, PhH O LDA, THF Me 89% O Me Me 1. LDA, MoOHPy Me H 2. Ph3P • • O Me H TBAF TMS 41% PhO S OH OH 2 OSitBuPh2 OH THPO THPO Tet. Lett. 1991, 32, 531 H J. Org. Chem. 1988, 53, 4855 H Baran Lab GM 08/13/2011 Organic Chemistry from the Eastern Bloc Florina Voica EtO2C Br O CO2Et Me Me HO Me LDA/THF, -78 °C then Me Br Br TMS TMS Me nBuLi, BF •Et O Me Me Me 3 2 Br iPr H 93% H 80% THPO THPO H H OMe OMe 1.VO(acac)2, TBHP, 86% 1. DIBAL 2. mCPBA, 87% 2. TsCl, pyr 3. TFAA, pyr, 87% 3. Superhydride 80% F3C O O O Br Br O Me Me Me Br Me Br TMS Me Me TBAF, H O, CHBr -50%NaOH 2 Me 3 Me THF, rt CETRIMID O O Me 50%, dr 1:1 Me H H (separable) THPO THPO H H OMe OMe MeLi/Et2O -78 °C to rt then MeI, -78 °C to rt 60% O O O Me Me Me OH Me Me Me Me Me Me Me Me TsOH/aq dioxane Me H OH OH THPO HO H H HO Digitoxigenin OMe 23-H-isocalysterol J. Org. Chem. 1995, 60, 1823 (both diastereoisomers are NPs) J. Am. Chem. Soc. 1995, 117, 1849 Baran Lab GM 08/13/2011 Organic Chemistry from the Eastern Bloc Florina Voica For more on steroid functionalization: J. Org. Chem. 2010, 75, 5388, J. Org. Chem. 1990, 55, 3484, NO2 tBuOK DMF/THF DMDO, Ph Tetrahedron 1989, 45, 2223, Tet. Lett. 1988, 29, 4001, J. Org. Chem. 1973, 38, 1280. Ph aq. NH4Cl -70 °C H2O For some representative refs on formal syntheses of different vitamin Ds (20 papers published)- + NC OH Tet. Lett. 1998, 29, 885, Synthesis 1999, 1209; J. Org. Chem. 2007, 72, 5276. NC Me Me For work on terpene synthesis: Tet. Lett. 2005, 46, 1149, J. Org. Chem. 2010, 75, 8337. 83% SO2Ph SO2Ph Prof. Mieczyslaw Makosza J. Org. Chem. 1998, 63, 4390 - born in 1934 N N N - education: Cl SO2Ph M. Sc : Univ.of Leningrad, 1958 66% Ph.D : Technical Univ. Warsaw, 1956 KOH, DMSO N D.Sc : Technical Univ. Warsaw, 1971 N N - positions: Chem. Lett. 1987, 61 1975-1977, Director, Institute of Organic Chemistry and Technology, SO2Ph Univ. of Warsaw TBSO O- NO + 1979-present, Director, Institute of Organic Chemistry, Polish Academy of 2 N Ph NO Ph Sciences. Ph DBU DBU - 420 publications (Scifinder) TBSCl -TBSOH - major research areas: phase transfer catalysis (chemistry of carbanions SO2 SO2 and carbenes), vicarious nucleophilic substitution. SO2 N N N Me Me Me Vicarious Nucleophilic Substitution of Hydrogen (VNS) - describes the reaction of a nucleophile with a electrophilic arene (nitroarenes, heteroarenes) or DBU alkene; TBSCl - the attack can occur ortho or para to the NO2 group but there are ways to achieve selectivity; DBU TBSO TBSO disubstituted prods are usually not observed; N N N - VNS is an "umpolung Friedel-Crafts" reaction and it complements the scope of the FC rxn since -TBSOH hν Ph it allows functionalization of arenes which are very poor nucleophiles in SEAr. General reaction scheme: SO2 SO2 SO2 N N N base Me Me Me base + R X solvent -HX H Acta Chem. Scand. 1992, 46, 689 + X OMe Y Y Y OH OH Y Me2SO4, MeO NO MeO NO MeO NO2 2 PhO CN 2 NaHCO3 NO NO - R NO - R NO R 2 2 2 2 83% tBuOK, DMF CN CN σH complex 80% Z = F, Cl, Br, I, OMe, OPh, SMe, Et, tBu, Ph, NMe2, CF3, CN, SO2Me, CO2H.
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