Heterocycle Construction: The Chang Synthesis of Louisianin C

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Acid Chloride ◽  
Diels Alder ◽  
Heinrich Heine ◽  
University Of Pittsburgh ◽  
Medical College ◽  
University Of Technology ◽  
Mcgill University ◽  
Acid Catalyzed ◽  
The University ◽  
Indole Synthesis

It has been known for some time that an acid chloride 1 can be added to an alkyne 2 to give the β-chloro enone. Yasushi Tsuji of Kyoto University found (J. Am. Chem. Soc. 2009, 131, 6668) that with an Ir catalyst, the condensation of 1 with 2 could be directed to the furan 3. Huanfeng Jiang of the South China University of Technology described (Organic Lett. 2009, 11, 1931) a complementary route to furans, Cu-mediated condensation of a propargyl alcohol 4 with the diester 5 to give 6. Bruce A. Arndtsen of McGill University developed (Organic Lett. 2009, 11, 1369) an approach to pyrroles such as 9, by condensation of an α,β-unsaturated α-cyano imine 7 with the acid chloride 8. Thomas J. J. Müller of Heinrich-Heine-Universität Düsseldorf observed (Organic Lett. 2009, 11, 2269) the condensation of an acid chloride 11 with a propargyl amine 10, leading to the iodo pyrrole 12. John A. Murphy of the University of Strathclyde uncovered (Tetrahedron Lett. 2009, 50, 3290) a new entry to the Fischer indole synthesis, by Petasis homologation of a hydrazide 13. Dali Yin of Peking Union Medical College took advantage (Organic Lett. 2009, 11, 637) of the easy sequential displacement of the fluorides of 15, leading, after acid-catalyzed cyclization, to the indole 17. Kang Zhao of Tianjin University extended (Organic Lett. 2009, 11, 2417; Organic Lett. 2009, 11, 2643) his studies of oxidation of an enamine 18 to the 2H -azirine, that on heating cyclized to the indole 19. Peter Wipf of the University of Pittsburgh established (Chem. Commun. 2009, 104) a microwave-promoted indole synthesis, illustrated by the intramolecular Diels-Alder cyclization of 20 to 21. A review delineating all nine types of indole syntheses will appear shortly in Angewandte Chemie . Fushun Liang and Qun Liu of Northeast Normal University demonstrated (J. Org. Chem. 2009, 74, 899) that the readily-prepared ketene thioacetal 22 condensed with NH3 to give the pyridine 23. Sundaresan Prabhakar and Ana M. Lobo of the New University of Lisbon observed (Tetrahedron Lett. 2009, 50, 3446) that the addition of the alkoxy propargyl amine to the alkyne 25 gave a Z alkene, that on warming rearranged to the pyridine 26.

John James Rickard Macleod, 1876-1935

1935 ◽  
Vol 1 (4) ◽  
pp. 584-589
Keyword(s):  
Royal Society ◽  
Early Death ◽  
Early Age ◽  
Grammar School ◽  
University Of Toronto ◽  
Medical College ◽  
Mcgill University ◽  
The University ◽  
University Of Leipzig ◽  
Regius Professor

John James Rickard Macleod, the son of the Rev. Robert Macleod, was born at Cluny, near Dunkeld, Perthshire, on September 6, 1876. He received his preliminary education at Aberdeen Grammar School and in 1893 entered Marischal College, University of Aberdeen, as a medical student. After a distinguished student career he graduated M.B., Ch.B. with Honours in 1898 and was awarded the Anderson Travelling Fellowship. He proceeded to Germany and worked for a year in the Physiological Institute of the University of Leipzig. He returned to London on his appointment as a Demonstrator of Physiology at the London Hospital Medical College under Professor Leonard Hill. Two years later he was appointed to the Lectureship on Biochemistry in the same college. In 1901 he was awarded the McKinnon Research Studentship of the Royal Society. At the early age of 27 (in 1902) he was appointed Professor of Physiology at the Western Reserve University, Cleveland, Ohio, a post he occupied until 1918, when he was elected Professor of Physiology at the University of Toronto. Previous to this transfer he had, during his last two years at Cleveland, been engaged in various war duties and incidentally had acted for part of the winter session of 1916 as Professor of Physiology at McGill University, Montreal. He remained at Toronto for ten years until, in 1928, he was appointed Regius Professor of Physiology in the University of Aberdeen, a post he held, in spite of steadily increasing disability, until his lamentably early death on March 16, 1935, at the age of 58.

Metal-Mediated C–C Ring Construction: (+)-Shiromool (Baran)

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Claisen Rearrangement ◽  
Enantiomeric Excess ◽  
Enantioselective Hydrogenation ◽  
Water Soluble ◽  
University Of Pittsburgh ◽  
Ru Catalyst ◽  
University Of Technology ◽  
La Jolla ◽  
The University ◽  
Medium Rings

Seiji Iwasa of the Toyohashi University of Technology devised (Adv. Synth. Catal. 2012, 354, 3435) a water-soluble Ru catalyst for enantioselective intramolecular cyclopropanation that could be separated from the product and recycled by simple water/ether extraction. Minoru Isobe of the National Tsing Hua University combined (Org. Lett. 2012, 14, 5274) the Nicholas and Hosomi-Sakurai reactions to close the cyclobutane ring of 4. Kazunori Koide of the University of Pittsburgh established (Tetrahedron Lett. 2012, 53, 6637) that the activity of a Ru metathesis catalyst, shut down by the presence of TBAF, could be restored by the inclusion of TMS2O. Jan Streuff of Albert-Ludwigs-Universität Freiburg demonstrated (Angew. Chem. Int. Ed. 2012, 51, 8661) that the enantiomerically pure Brintzinger complex mediated the reductive cyclization of 7 to 8. Huw M.L. Davies of Emory University prepared (J. Am. Chem. Soc. 2012, 134, 18241) the cyclopentenone 11 by the Rh-mediated addition of 10 to 9 followed by elimination. Christophe Meyer and Janine Cossy of ESPCI ParisTech showed (Angew. Chem. Int. Ed. 2012, 51, 11540) that the Rh-mediated rearrangement of 12 to 13 proceeded with substantial diastereocontrol. Jian-Hua Xie and Qi-Lin Zhou of Nankai University observed (Org. Lett. 2012, 14, 6158) that the enantioselective hydrogenation of 14 followed by Claisen rearrangement established the cyclic quaternary center of 17 with high stereocontrol. Ken Tanaka of the Tokyo University of Agriculture and Technology devised (Angew. Chem. Int. Ed. 2012, 51, 13031) the Rh-mediated addition of the enyne 18 to 19 to give the highly substituted cyclohexene 20. Daesung Lee of the University of Illinois at Chicago showed (Chem. Sci. 2012, 3, 3296) that the ring-opening/ring-closing metathesis of 21 delivered 22 with high diastereocontrol. Andreas Speicher of Saarland University cyclized (Org. Lett. 2012, 14, 4548) 23 to 24 with significant atropisomeric induction. Erick M. Carreira of the Eidgenössische Technische Hochschule Zürich effected (J. Am. Chem. Soc. 2012, 134, 20276) the polycyclization of racemic 25 to 26 with high enantiomeric excess. Medium rings are often the most difficult to construct, because of the inherent congestion across the forming ring. Phil S. Baran of Scripps/La Jolla effected (Angew. Chem. Int. Ed. 2012, 51, 11491) the cyclization of 27 to 28 as a single dominant diastereomer.

Alkaloid Synthesis: (–)-α-Kainic Acid (Cohen), Hyacinthacine A2 (Fox), (–)-Agelastatin A (Hamada), (+)-Luciduline (Barbe), (+)-Lunarine (Fan), (–)-Runanine (Herzon)

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Kainic Acid ◽  
Aldol Condensation ◽  
Catalyst System ◽  
Diels Alder ◽  
Yale University ◽  
University Of Pittsburgh ◽  
Agelastatin A ◽  
Alkaloid Synthesis ◽  
Carbocyclic Rings ◽  
The University

The intramolecular ene cyclization is still little used in organic synthesis. Theodore Cohen of the University of Pittsburgh trapped (J. Org. Chem. 2011, 76, 7912) the cyclization product from 1 with iodine to give 2, setting the stage for an enantiospecific total synthesis of (–)-α-kainic acid 3. Intramolecular alkene hydroamination has been effected with transition metal catalysts. Joseph M. Fox of the University of Delaware isomerized (Chem. Sci. 2011, 2, 2162) 4 to the trans cyclooctene 5 with high diastereocontrol. Deprotection of the amine led to spontaneous cyclization, again with high diastereocontrol to hyacinthacine A2 6. Yasumasa Hamada of Chiba University devised (Org. Lett. 2011, 13, 5744) a catalyst system for the enantioselective aziridination of cyclopentenone 7. The product 8 was carried on to the tricyclic alkaloid (–)-agelastatin A 9. Guillaume Barbe, now at Novartis in Cambridge, MA, effected (J. Org. Chem. 2011, 76, 5354) the enantioselective Diels-Alder cycloaddition of acrolein 11 to the dihydropyridine 10. Ring-opening ring-closing metathesis later formed one of the carbocyclic rings of (+)-luciduline 13, and set the stage for an intramolecular aldol condensation to form the other. Chun-An Fan of Lanzhou University employed (Angew. Chem. Int. Ed. 2011, 50, 8161) a Cinchona-derived catalyst for the enantioselective Michael addition to prepare 14. Although 14 and 15 were only prepared in 77% ee, crystallization to remove the racemic component of a later intermediate led to (+)-lunarine 16 in high ee. Seth B. Herzon of Yale University used (Angew. Chem. Int. Ed. 2011, 50, 8863) the enantioselective Diels-Alder addition with 18 to block one face of the quinone 17. Reduction of 19 followed by methylation delivered an iminium salt, only one face of which was open for the addition of an aryl acetylide. Thermolysis to remove the cyclopentadiene gave an intermediate that was carried on to (+)-runanine 20.

Developments in Alkene Metathesis

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Large Scale ◽  
Cross Coupling ◽  
National Chemical Laboratory ◽  
Chemical Laboratory ◽  
Metal Centers ◽  
University Of Pittsburgh ◽  
University Of Technology ◽  
Alternative Approach ◽  
Catalyzed Reactions ◽  
The University

Alkene metathesis has been extended to increasingly complex starting materials and products. Nitriles are good donors to coordinatively-unsaturated transition metal centers, so tend to inhibit the reaction. Ren He of Dalian University of Technology has found (Tetrahedron Lett. 2007, 48, 4203) that inclusion of the loosely-coordinating 2-methyl pyridine in the reaction enables facile cross-coupling with acrylonitrile 2. Although crosscoupling with (Z, Z)-sorbate is not efficient, Dennis P. Curran of the University of Pittsburgh has shown (Organic Lett. 2007, 9, 5) that cross-coupling with (E, Z)-sorbate 5 works well. For large scale work, he has developed a Hoveyda-type catalyst with a perfluoro tail, that is recoverable in 70% recrystallized yield from the reaction mixture. Shigefumi Kuwahara of Tohoku University has reported (Tetrahedron Lett. 2007, 48, 3163) a practical alternative for direct metathesis to deliver (E, E)-dienyl esters. Continuing the investigation of tandem Ru-catalyzed reactions, Marc L. Snapper of Boston College effected (Organic Lett. 2007, 9, 1749) metathesis with methacrolein 8a, then added Ph3P and diazoacetate, to give the diene 11. A range of common Ru catalysts worked well for this transformation. In an alternative approach to trisubstituted alkene construction, Stellios Arseniyadis and Janine Cossy of ESPCI Paris have demonstrated (Organic Lett. 2007, 9, 1695) that inclusion of Cl-catecholborane 14 allows clean cross metathesis with the lactone 13. The construction of tetrasubstituted alkenes has been more challenging. Yann Schrodi of Materia, Inc. (Organic Lett. 2007, 9, 1589) has described a catalyst 17 that is particularly effective. Complex 17 was superior to a catalyst reported (Organic Lett. 2007, 9, 1339) shortly earlier by Robert H. Grubbs of Caltech. Debendra K. Mohapatra of the National Chemical Laboratory, Pune, and Professor Grubbs, in a new approach to macrocyclic stereocontrol, have made (Tetrahedron Lett. 2007, 48, 2621) the remarkable observation that the cyclization of the bis ether 19a gave 20 in a 9:1 E / Z ratio, while cyclization of the diol 9b gave only Z - 21. Oligomer formation can often compete in such medium ring-forming reactions. Deryn E. Fogg of the University of Ottawa has raised (J. Am. Chem. Soc. 2007, 129, 1024) the cautionary (but happy!) observation that while the cyclization, for instance, of 22 proceeded efficiently to give 23, at an intermediate point in the transformation the product was more than half oligomer.

The Center for International Biomedical Communications Research

1966 ◽  
Vol 05 (03) ◽  
pp. 142-146
Author(s):  
A. Kent ◽  
P. J. Vinken
Keyword(s):  
Information Needs ◽  
English Language ◽  
Medical Information ◽  
Biomedical Literature ◽  
Information Storage ◽  
Control Mechanisms ◽  
University Of Pittsburgh ◽  
The World ◽  
The University ◽  
Excerpta Medica Foundation

A joint center has been established by the University of Pittsburgh and the Excerpta Medica Foundation. The basic objective of the Center is to seek ways in which the health sciences community may achieve increasingly convenient and economical access to scientific findings. The research center will make use of facilities and resources of both participating institutions. Cooperating from the University of Pittsburgh will be the School of Medicine, the Computation and Data Processing Center, and the Knowledge Availability Systems (KAS) Center. The KAS Center is an interdisciplinary organization engaging in research, operations, and teaching in the information sciences.Excerpta Medica Foundation, which is the largest international medical abstracting service in the world, with offices in Amsterdam, New York, London, Milan, Tokyo and Buenos Aires, will draw on its permanent medical staff of 54 specialists in charge of the 35 abstracting journals and other reference works prepared and published by the Foundation, the 700 eminent clinicians and researchers represented on its International Editorial Boards, and the 6,000 physicians who participate in its abstracting programs throughout the world. Excerpta Medica will also make available to the Center its long experience in the field, as well as its extensive resources of medical information accumulated during the Foundation’s twenty years of existence. These consist of over 1,300,000 English-language _abstract of the world’s biomedical literature, indexes to its abstracting journals, and the microfilm library in which complete original texts of all the 3,000 primary biomedical journals, monitored by Excerpta Medica in Amsterdam are stored since 1960.The objectives of the program of the combined Center include: (1) establishing a firm base of user relevance data; (2) developing improved vocabulary control mechanisms; (3) developing means of determining confidence limits of vocabulary control mechanisms in terms of user relevance data; 4. developing and field testing of new or improved media for providing medical literature to users; 5. developing methods for determining the relationship between learning and relevance in medical information storage and retrieval systems’; and (6) exploring automatic methods for retrospective searching of the specialized indexes of Excerpta Medica.The priority projects to be undertaken by the Center are (1) the investigation of the information needs of medical scientists, and (2) the development of a highly detailed Master List of Biomedical Indexing Terms. Excerpta Medica has already been at work on the latter project for several years.

MAKING IT GREEN: THE FOOD PACKAGING PERCEPTIONS AND PRACTICES OF YOUNG CONSUMERS

2019 ◽  
Vol 1 (1) ◽  
pp. 28
Author(s):  
Norsyamira Shahrin ◽  
Rabiatul Adawiyah Abd Rahman ◽  
Noorliza Zainol ◽  
Noor Saliza Salmi ◽  
Mohd Faisal Abdul Wahab
Keyword(s):  
Standard Deviation ◽  
Food Packaging ◽  
Food Handler ◽  
Polystyrene Foam ◽  
University Of Technology ◽  
Young Consumers ◽  
Plastic Bag ◽  
The Government ◽  
The University

Food handler still fails to play their part even when the government imposes “No Plastic Bag” campaign and a ban on polystyrene foam to pack foods. This research focuses on eco-friendly food packaging based on the perception and practice of young consumers, especially the undergraduates of Mara University of Technology Penang Campus (UiTMPP). Questionnaire was constructed and distributed to 315 respondents.  The collected data were analyzed with simple descriptive statistic of frequency, mean and standard deviation. Most of the respondents are aware on eco-friendlyfood packaging. They agreed that the university should propose some alternative to control and reduce non-biodegradable foods packaging. 

Numerical Modeling of the RDE

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Michal Folusiak ◽  
Karol Swiderski ◽  
Piotr Wolański
Keyword(s):  
Combustion Chamber ◽  
Turbine Engine ◽  
Rotating Detonation Engine ◽  
University Of Technology ◽  
Detonation Combustion ◽  
Detonation Engine ◽  
Innovative Economy ◽  
Turboshaft Engine ◽  
The University ◽  
Rotating Detonation

AbstractThe idea of using the phenomenon of rotating detonation to propulsion has its roots in fifties of the last century in works of Adamson et al. and Nicholls et al. at the University of Michigan. The idea was recently reinvented and experimental research and numerical simulations on the Rotating Detonation Engine (RDE) are carried in numerous institutions worldwide, in Poland at Warsaw University of Technology (WUT) since 2004. Over the period 2010-2014 WUT and Institute of Aviation (IOA) jointly implemented the project under the Innovative Economy Operational Programme entitled ‘Turbine engine with detonation combustion chamber’. The goal of the project was to replace the combustion chamber of turboshaft engine GTD-350 with the annular detonation chamber.This paper is focused on investigation of the influence of a geometry and flow conditions on the structure and propagation stability of the rotating detonation wave. Presented results are in majority an outcome of the aforementioned programme, in particular authors’ works on the development of the in-house code REFLOPS USG and its application to simulation of the rotating detonation propagation in the RDE.

Thyrsa Wealtheow Amos: The Dean of Deans

NASPA Journal ◽  
2004 ◽  
Vol 41 (2) ◽  
Author(s):  
Richard J. Herdlein
Keyword(s):  
Higher Education ◽  
Student Affairs ◽  
Historical Research ◽  
University Of Pittsburgh ◽  
Student Personnel ◽  
Dean Of Women ◽  
History Of ◽  
Personnel Administration ◽  
The University

The scholarship of student affairs has neglected to carefully review its contextual past and, in the process, failed to fully integrate historical research into practice. The story of Thyrsa Wealtheow Amos and the history of the Dean of Women’s Program at the University of Pittsburgh,1919–41, helps us to reflect on the true reality of our work in higher education. Although seemingly a time in the distant past, Thyrsa Amos embodied the spirit of student personnel administration that shines ever so bright to thisd ay. The purpose of this research is to provide some of thatcontext and remind us of the values that serve as foundations of the profession.

scholarly journals Bariatric Surgery vs Lifestyle Intervention for Diabetes Treatment: 5-Year Outcomes From a Randomized Trial

2020 ◽  
Vol 105 (3) ◽  
pp. 866-876 ◽  
Author(s):  
Anita P Courcoulas ◽  
James W Gallagher ◽  
Rebecca H Neiberg ◽  
Emily B Eagleton ◽  
James P DeLany ◽  
...  
Keyword(s):  
Bariatric Surgery ◽  
Weight Loss ◽  
Lifestyle Intervention ◽  
Controlled Trial ◽  
The United States ◽  
Diabetes Remission ◽  
University Of Pittsburgh ◽  
Lifestyle Treatment ◽  
Surgical Treatments ◽  
The University

Abstract Context Questions remain about bariatric surgery for type 2 diabetes mellitus (T2DM) treatment. Objective Compare the remission of T2DM following surgical or nonsurgical treatments. Design, setting, and participants Randomized controlled trial at the University of Pittsburgh, in the United States. Five-year follow-up from February 2015 until June 2016. Interventions 61 participants with obesity and T2DM who were initially randomized to either bariatric surgical treatments (Roux-en-Y gastric bypass [RYGB] or laparoscopic adjustable gastric banding [LAGB]) or an intensive lifestyle weight loss intervention (LWLI) program for 1 year. Lower level lifestyle weight loss interventions (LLLIs) were then delivered for 4 years. Main Outcomes and Measures Diabetes remission assessed at 5 years. Results The mean age of the patients was 47 ± 6.6 years, 82% were women, and 21% African American. Mean hemoglobin A1c level 7.8% ± 1.9%, body mass index (BMI) 35.7 ± 3.1 kg/m2, and 26 participants (43%) had BMI < 35 kg/m2. Partial or complete T2DM remission was achieved by 30% (n = 6) of RYGB, 19% (n = 4) of LAGB, and no LWLI participants (P = .0208). At 5 years those in the RYGB group had the largest percentage of individuals (56%) not requiring any medications for T2DM compared with those in the LAGB (45%) and LWLI (0%) groups (P = .0065). Mean reductions in percent body weight at 5 years was the greatest after RYGB 25.2% ± 2.1%, followed by LAGB 12.7% ± 2.0% and lifestyle treatment 5.1% ± 2.5% (all pairwise P < .01). Conclusions Surgical treatments are more effective than lifestyle intervention alone for T2DM treatment.

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