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Abstract

In Chapter 1, natural product synthesis is pursued toward strained, stereochemically-rich polycyclic skeletons in the dankasterone and illisimonin families. Key motifs targeted include contiguous 4° stereocenters and multiple trans-cyclopentaoid units within a strained polycyclic core. High yields and diastereoselectivity are accomplished in the ultimate convergent strategy toward dankasterones A and B. Meanwhile, methodological efforts are described toward both the common 2,6-disubstituted piperidine motif via a Mannich-type reaction and the enormous organobromine family via bromonium-induced cyclization. The described efforts seek to expand the available options for access to synthetically desirable bioactive motifs. Zooming out from Chapter 1’s focus on the outcome of individual chemical reactions, Chapters 2 – 3 characterize the environment in which this chemistry occurs, revealing commonalities and challenges associated with the oft-obscured details of conducting successful benchwork. In Chapter 2, the chemistry research environment itself is examined, first through phenomenological observational case studies characterizing the nature of benchwork followed by psychometric measurement of chemistry safety behavior in Chapter 3. These qualitative and quantitative methodologies respectively provide novel benchmarks for the chemistry community in understanding how chemistry research itself is conducted. Such detailed portraits then enable evidence-based discussions on how to more efficiently and effectively support successful chemistry research. In Chapter 4, the process of learning how to do bench chemistry is explored through an exhaustive scoping literature review on lab-based learning during the COVID-19 pandemic. When considered in conjunction with the findings from the preceding chapters, the review exposes areas of misalignment regarding current paradigms for lab-based learning versus the intellectual and physical demands of the chemistry research environment. Taken together, these chapters reveal the complexity of lab-based learning and prompt re-consideration of a one-size-fits-all modality of laboratory instruction. Finally, Chapters 5 – 6 address the network nature of chemistry research, the doing of chemistry, and the teaching and learning of chemistry by analyzing the apprenticeship backdrop of laboratory research training. A survey instrument is constructed and validated to evaluate the core tenants of chemistry research mentorship across trainee levels (i.e., undergraduate students -> postdoctoral researchers) in Chapter 5. Meanwhile, departmental structures for supporting continuing professional development via seminars are subjected to comparative value-added analysis in Chapter 6. Considering that the current model of chemistry research training has remained mostly unchanged for over a century, evaluating the strengths and weaknesses of these training models may enable timely adjustments for the next generation of trainees.

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