Event Information
Using Organic Chemistry to Evaluate Hypotheses of Spontaneous Biosynthetic Events
- Abstract:
Hypothesis statements: Natural product biosynthesis through a pathway that involves a non-enzymatic reaction is more common than generally thought. The reactant is often a late-stage biosynthetic intermediate that is produced by ubiquitous (common) classes of enzymes and reaction pathways. This intermediate coincidentally happens to have been endowed with sufficiently high internal reactivity that it further converts (i.e., reacts), intramolecularly and spontaneously, under the ambient conditions of the producing organism. Consequences of such a reaction are i) that it often leads to a considerable increase in structural complexity and ii) that the resultant natural product typically describes a rare, if not unique, structural class.
Hypotheses of spontaneous reactivity are often testable by synthesis, and this thinking is driving a number of current studies in our laboratories. I will discuss three of these studies, from the perspectives of both synthetic and mechanistic organic chemistry, in the specific context of natural products 1–3. I will also discuss how the last of these has led to a serendipitous (re?)discovery of a new type of Diels-Alder reaction.
Host: Ross Widenhoefer
Chemistry Seminar