Blasting Off to a Bright Future

The total synthesis of racemic Rosiglitazone, also known as the anti-diabetes drug Avandia, in six steps is the basis for an advanced undergraduate organic chemistry laboratory course. Several techniques and concepts learned in an introductory organic chemistry laboratory course are reinforced, and include TLC analysis, recrystallization, and reaction work-up. Additional techniques introduced into the organic chemistry laboratory course include phase-transfer catalysis, flash column chromatography, pressurized hydrogenation reactions, and multi-step total synthesis. Students are challenged at several levels, but mostly by an expectation of independent, in-depth spectral analysis of each product and providing bi-weekly experimental reports with journal-style spectral analysis. An advanced undergraduate organic laboratory course centered on the total synthesis of a medicinally important compound provides an overall focus for the semester, as well as greater interest and motivation for students.

California Section. Consultant, LHLatimer Consulting, Oakland, California. Academic record: Tulane University, BS, chemistry, 1971; University of Wisconsin, PhD, organic chemistry, 1976; University of California, Berkeley, postdoctoral research in organic chemistry, 1976–77; University of Wisconsin School of Pharmacy, postdoctoral research in organic chemistry, 1977–79. Honors: ACS Division of Chemical Health and Safety, Howard Fawcett Chemical Health Award, 2016; ACS Santa Clara Valley Section, Shirley B. Radding Award, 2014; ACS Fellow, 2012; ACS California Section, Walter B. Petersen Award, 2010; ACS Rochester Section, Rochester Section Award, 1991; Elan Pharmaceuticals, Chemical Sciences Excellence Award, 2009; Kodak Research Labs, Gold Team Achievement Award, 1992; National Institutes of Health, Postdoctoral Fellowship, 1977–79; Phi Beta Kappa, 1971; Sigma Xi, 1971. Professional positions (for past 10 years): LHLatimer Consulting, drug development consultant, 2011–; NeurOp, head of chemistry, 2014–16; Elan Pharmaceuticals, 1995–2011, senior director of process and analytical chemistry, 2005–11, chemical hygiene officer, 2004–10; San Francisco State University,

Information processing is a very fundamental activity in research, probably more important than most of us realize. Research is begun based on previously established information and the product of research is also information. This output information results from experimental observations or combinations of and extrapolations from previous information. The majority of information processed, for example, by a chemist in research is non-numerical — symbols, words, relations, logical inference, etc.1 Numeric symbols and the common arithemetic operations are simply a small subset of what we need for information processing in research. It is only in the last decade that programming languages (eg. LISP) have been developed which enable one to easily manipulate symbolic representations within a computer, enabling one to begin applying computers to some of the more interesting non-numerical problems in science. The elegant work Buchanan presented at this meeting in structure elucidation is an example of what has been done in this area. In this paper I wish to focus on computer-assisted planning of research in organic chemistry in general. As illustrations, I will refer to recent applications in synthesis, mechanistic studies, and biogenesis.

Many cities in the world were placed under various lockdowns to combat the spread of the COVID-19 pandemic, which also forced many schools to shift into full online mode of teaching and learning. In the Philippines, partial onsite classes only resumed after nearly 2 years of strict online classes. Of critical concern then was the teaching of laboratory courses. This necessitated the re-design of the usual laboratory experiments to a Lab@Home course to provide a semester’s worth of an organic laboratory course to college students of the Ateneo de Manila University. Here, we present a Lab@Home curriculum that covers core organic chemistry concepts, such as purification and separation of organic compounds, reactivity and qualitative tests, stereochemistry, and molecular spectroscopy (IR and NMR). This Lab@Home course involved sending boxed kits containing laboratory materials and reagents that allowed students at home to perform small-scale experiments. Aside from reinforcing key concepts in the accompanying lecture class, it also provided them with experiential learning of practical laboratory techniques such as setting up an experiment and real data collection. Safety first is maintained, and aside from providing the usual protective gear, safety is further assured with two important features: (1) the hazards classification of the reagents in the kit would not exceed the everyday life hazards of common household chemicals (e.g., kitchen cleaning reagents) and provided in very small amounts, and (2) running of experiments were done with online synchronous supervision majority of the time. The success of the course is the achievement of the CLOs, from the assessments as well as from feedback taken from surveys and interviews with students and instructors at the end of the semester. Overall student performance showed an average final grade of 85%, and student response to the curriculum was generally positive. Further improvements should be implemented to make experiments more enriching and ensure Lab@Home can become an effective tool for teaching remote laboratory classes.

A Positron Emission Tomograph based on LSO-APD modules with a sampling ADC read-out system for a students’ advanced laboratory course

In the few years since its discovery, gas chromatography has revolutionized the conduct of research in organic chemistry and biochemistry. Its application to problems in inorganic chemistry has been slower in coming, but it is now clear that gas chromatography has much to offer to the inorganic chemist as well. For a more detailed discussion, bibliography, and historical development of inorganic studies, the reader is referred to the book entitled Gas Chromatography of Metal Chelates. Many more recent papers are listed in Ref. 2 and 3.

An advanced laboratory course for physics seniors is described that uses open-ended projects organized in such a way that all of the students work on each project in turn. The students change every two or three weeks from one project to another, each time being confronted with an ongoing experiment to which they are asked to make their contribution. The laboratory notebooks contain the cumulative total of a group effort. Individual experiments can be carried to considerable depth, but at the same time the individual students are not confined to the limitations of working on just one project.

A thoughtful approach to designing and improving labs, particularly at the advanced level, is critical for the effective preparation of physics majors for professional work in industry or graduate school. With that in mind, physics education researchers in partnership with the physics faculty at the University of Colorado Boulder have overhauled the senior-level Advanced Physics Lab course. The transformation followed a three part process of establishing learning goals, designing curricula that align with the goals, and assessment. Similar efforts have been carried out in physics lecture courses at the University of Colorado Boulder, but this is the first systematic research-based revision of one of our laboratory courses. The outcomes of this effort include a set of learning goals, a suite of new lab-skill activities and transformed optics labs, and a set of assessments specifically tailored for a laboratory environment. While the particular selection of advanced lab experiments varies widely between institutions, the overall transformation process, the learning goals, and the assessments are broadly applicable to the instructional lab community.

THE Royal Commission for the Exhibition of 1851 announces the award of senior studentships for 1946 to the following: On the recommendation of the University of Cambridge: Mr. G. K. Batchelor (of Melbourne and Cambridge), for research in applied mathematics at Cambridge ; Dr. C. J. Eliezer (of Ceylon and Cambridge), for research in theoretical physics at Cambridge ; and Mr. C. H. Hassall (of New Zealand and Cambridge), for research in organic chemistry at Cambridge. On the recommendation of the University of Oxford: Dr. R. P. Penrose (Oxford), for research in experimental physics at Oxford.

For more than a century heterocycles have constituted one of the largest areas of research in organic chemistry. The heterocyclic moieties are of exceptional interest in the pharmaceutical industry as they make up a core part of several drugs. The importance of heterocycles provides a significant basis for the development of new methods for their synthesis. Further, due to the strengthening environmental regulations and safety concerns, the industries are in need of new innovative, environmental friendly alternate routes for synthesizing the therapeutic and pharmacological important heterocyclics are desired. This environmentally benign synthesis can be easily designed using microwave methodology. The microwaves induce rapid heating and avoid the harsh classical conditions, resulting in the formation of cleaner products. The first chapter thus deals with the microwave theory, latest developments in instrumentation technology, the various microwave technologies used for synthesis.

Stereoselective nucleophilic additions to α-substituted carbonyl compounds are a crucial area of contemporary research in organic chemistry. Of the various advancements in π-facial selectivity in addition reactions of carbonyl compounds, the (polar) Felkin-Anh model and the chelation model are well recognized for accurately explaining the selectivity of the allylic products. For reactions that involve α-oxy carbonyl groups - known for their broad applications in natural-product synthesis and as effective building blocks in organic synthesis - the stereoselective reaction typically follows the chelation model, favoring syn-selective addition. In contrast to the well-established syn-selective additions of α-oxy carbonyls, anti-selective additions through a non-chelation pathway remain largely unexplored. In this study, we present the anti-selective allylation of α-oxy ketones using allylatranes that feature a highly coordinated group-14-element center. These atranes demonstrate high nucleophilicity and low chelating ability due to their transannular interactions and rigid framework, facilitating anti-selective allylations. A combined experimental and theoretical approach has been used to highlight the unique electronic properties of these atranes. This method is applicable to a wide variety of substrates, producing anti-1,2-diols with a homoallylic moiety in high yield and excellent diastereoselectivity compared to traditional methods.

Efficient catalytic reactions that generate C–C bonds enantioselectively and those that produce trisubstituted alkenes diastereoselectively are central to research in chemistry. Transformations that accomplish these two tasks simultaneously in a single operation are prized, particularly if the catalysts, substrates and reagents are easily accessed at low cost and reaction conditions are mild. Here, we report a facile multicomponent catalytic process that begins with a chemo-, site- and diastereoselective copper–boron addition to a mon-substituted allene; the resulting boron-substituted organocopper intermediates then participate in a chemo-, site- and enantioselective allylic substitution. Products, which contain a stereogenic carbon center, a mono-substituted alkene and an easily modifiable Z-trisubstituted alkenylboron group, are obtained in up to 89% yield, with >98% branch- and stereoselectivity and >99:1 enantiomeric ratio. The copper-based catalyst is derived from a robust heterocyclic salt that can be prepared in multi-gram quantities from inexpensive starting materials and without costly purification procedures. Utility of the approach is showcased through enantioselective synthesis of gram quantities of natural products rottnestol (member of an antibiotic family) and herboxidiene/GEX1A (anti-tumor).

A lifetime journey into the world of chemistry

This paper describes ongoing developments to an advanced laboratory course at Kettering University, which is targeted to students in engineering and engineering physics and emphasizes theoretical, computational, and experimental components in the context of airborne acoustics and modal testing [cf. D. A. Russell and D. O. Ludwigsen, J. Acoust. Soc. Am. 131, 2515-2524 (2012)]. These developments have included a transition to electronic laboratory notebooks and cloud-based computing resources, incorporation of updated hardware and software, and creation and testing of a multiple-choice assessment instrument for the course. When Kettering University suddenly shifted to exclusively remote teaching in March 2020 due to the COVID-19 pandemic, many of these changes proved to be essential for enabling rapid adaptation to a situation in which a laboratory was not available for the course. Laboratory activities were rewritten by crowdsourcing archived data, videos were incorporated to illustrate dynamic phenomena, and computer simulations were used to retain student interactivity. The comparison of multiple measures, including the assessment instrument, team-based grades on project papers, and individual grades on final exams, indicates that most students were successful at learning the course material and adapting to work on team-based projects in the midst of challenging remote learning conditions.

In this experiment, undergraduate students of an advanced laboratory course are introduced to dynamic nuclear magnetic resonance spectrocopy (NMR). The students used pulsed-field gradient methods (PFG-NMR) to measure the diffusion coefficient (D) of components of micelle solutions containing solubilizates (alcohols) with varying alkyl chain length. From the data obtained, the partition coefficient (P) of the alcohols between the aqueous and micelle phases was calculated and the effect of alkyl chain length on P is elucidated. Students used the diffusion coefficients of the micelles to calculate radii and compared the PFG-NMR results with those obtained from dynamic light scattering (DLS) experiments.