Natural products obtained from diverse sources are invariably endowed with some level of pharmacological activity. In the best cases, they may possess life-saving properties as marketed drugs exemplified by potent antitumor agents. A survey of architecturally complex bioactive molecules synthesized over the past two decades reveals the prowess of the synthetic chemist. In most instances, the focus of the synthesis has been on the attainment of the target molecule while highlighting one or more key chemical steps. Total synthesis also makes available small quantities of natural products, otherwise isolated in very limited amounts, for biological testing. Planning the relevant steps toward the synthesis of a target molecule involves many factors that may be critical to a successful outcome. The Why, What and How of organic synthesis will be discussed in the context of the subliminally perceived thoughts and images that generate ideas leading to discovery or to an unexpected result. Examples from total syntheses of natural products will serve to illustrate the conceptual basis of how ideas are generated and applied to the realization of a proposed synthesis.

Art, craft, logic, and the unforeseen in natural product synthesis

2019 Spring National Meeting

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