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Accumulating a foundation
Full Title: “Accumulating” a foundation: The philosophy behind organic cumulative exams1 Michael Jordan, the greatest basketball player of all time, put it best when he said, “Get the fundamentals down and the level of everything you do will rise.” Cumulative exams are about setting the foundation for your training. They are a signature part of […]
Fischer Fool-Proof: Lessons from Stereochemistry’s Shining Debut
An explication of Fischer’s proof for the configuration of sugars is the capstone lecture in sophomore organic chemistry. This feat of experimentation and logic offers lessons that are of broad utility beyond organic chemistry.
Hypocrellin A, With a Twist
Some time ago my research group stumbled upon a family of macrocycles whose structure contained a somewhat uncommon stereogenic element, a plane of chirality. A plane of chirality arises when restricted rotation around a planar unit in a molecule leads to the formation of stereoisomers. The textbook example (seriously, look at Eliel) is E-cyclooctene. The […]
Still Working Toward Convergence in Total Synthesis
I was at the Natural Products and Bioactive Compounds Gordon Research Conference (GRC) last summer. During the usual free time one afternoon, there was a roundtable discussion about the challenges faced by women in science and strategies to overcome those challenges. The conversation was promoted by the GRC organization, which made sure there was an […]
How to Organize your Orgo Lecture Notebook
With the hope of sharing best-practices for success in introductory orgo lecture, I asked an undergrad in my department (John Ovian) what he recommended. He gave me a sheet that explained how he organized his notebook and how his notebook became a valuable tool for studying. Those notes, plus some design inspiration from the […]
A Chocolate Bloom Analogy for Crumbling Concrete in Home Foundations*
Have you ever unwrapped a piece of chocolate only to find it has a whitish powder surrounding it? It almost stops you from eating the chocolate, right? Chocolate that gets the whitish powdery appearance is said to have undergone a bloom – called chocolate bloom. Fast temperature changes or exposure to moisture can hasten the […]
Diazonamide dot-com
I was at a conference this summer where Patrick Harran gave a lecture on his group’s approach toward the synthesis of callyspongiolide. It was special. Harran has charisma that, as best as I can gather, comes from a combination of a near photographic memory, tremendous creativity, deference to the contributions others in his field, and […]
How VanA Strains Get Away With It, Part Two
An evaluation of the thermodynamics of binding between various ligands of Vancomycin (Part 2/2) by Matthew Guberman-Pfeffer* Part 1 in this series can be found here on The Offset and also at the Winnower. Vancomycin Molecular Recognition Events (cont’d) Conversion of the C-terminal D-Ala to D-Lac in the bacterial peptide target results in the loss of one […]
Friendly Conversation
Some of the most rewarding moments in my professional career have been in the midst of protracted conversation with a colleague about some concept or how to communicate an idea to an audience. At times I’ve been the teacher and other times the learner, but the best is when somehow, almost through the strength of […]