A Chemistry Cascade: From Physical Organic Studies of Alkoxy Radicals to Alkaloid Synthesis

• Published in: Journal of organic chemistry Vol. 74; no. 17; pp. 6421 - 6441
• Main Author: Padwa, Albert
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 04.09.2009
• Subjects: Alkaloids - chemical synthesis; Alkaloids - chemistry; Animals; Chemistry; Chemistry, Organic - history; Chemistry, Organic - methods; Coleoptera; Exact sciences and technology; Female; Furans - chemistry; General and physical chemistry; Heterocyclic compounds; History, 20th Century; History, 21st Century; Kinetics and mechanisms; Molecular Structure; Nitrogen - chemistry; Organic chemistry; Padwa Albert; Photochemistry; Photochemistry - methods; Physical chemistry of induced reactions (with radiations, particles and ultrasonics); Preparations and properties; Reactivity and mechanisms; Reaction intermediate; Intramolecular reaction; 1,3-Dipolar cycloaddition; Catalytic reaction; Alkoxyl; Nitrogen heterocycle; Furan derivatives; Oxygen heterocycle; Biological activity; Organic sulfide; Alkaloid; Carbonyl Compounds; Diazo compound; Chemical synthesis; Rhodium II; Photochemistry; Photoexcitation; Successive reaction
• ISSN: 0022-3263; 1520-6904; 1520-6904
• DOI: 10.1021/jo901300x

In this Perspective, I present a personal account of a succession of chemical projects that I was involved with, each of which triggered or initiated my next research undertaking. It started with my early work in the field of physical organic photochemistry, which, in turn, guided me to my current research dealing with the synthesis of biologically active alkaloids. The article highlights some of the dominant themes of my research program over the past 48 years. Subject matter that is discussed includes the generation of reactive intermediates by photoexcitation, [1,3]-dipolar cycloaddition chemistry, rhodium(II)-catalyzed domino reactions of α-diazo carbonyl compounds, intramolecular [4 + 2]-cycloaddition of 2-amidofurans, and the utilization of various thio fragments for the synthesis of nitrogen heterocycles.