4910-62-7Relevant articles and documents
Biogenesis-Guided Synthesis and Structural Revision of Sarocladione Enabled by Ruthenium-Catalyzed Endoperoxide Fragmentation
Ning, Yuhan,Tian, Hailong,Gui, Jinghan
supporting information, p. 11222 - 11226 (2021/04/19)
Sarocladione is the first 5,10:8,9-diseco-steroid with a 14-membered macrocyclic diketone framework to have been isolated from a natural source. Herein we report a biomimetic synthesis of sarocladione in only two or seven steps from inexpensive, commercially available ergosterol. The key feature of this synthesis was a novel ruthenium-catalyzed endoperoxide fragmentation, which transformed various saturated endoperoxides into olefinic diketones by cleavage of two C?C bonds. This synthesis allowed us to unambiguously determine the structure of sarocladione and provided experimental support for its revised biosynthetic origin. This work also vividly demonstrates that consideration of the biogenesis is a powerful tool for elucidating the structures of natural products.
Light-Stabilized Dynamic Materials
Houck, Hannes A.,Blasco, Eva,Du Prez, Filip E.,Barner-Kowollik, Christopher
supporting information, p. 12329 - 12337 (2019/08/27)
The light-responsive adaptation of polymer materials typically requires different wavelengths or additional heat to induce reversible covalent bond formation and dissociation. Here, we bypass the use of invasive triggers by introducing light-stabilized dynamic materials that can undergo a repeatable change in topology from a covalently cross-linked material into a liquid polymer formulation by switching one visible light source on-and-off without the need for any additional triggers. Specifically, we exploit the photo-Diels-Alder reaction of triazolinediones with naphthalenes as a dynamic covalent cross-linking platform that enables green light-induced network formation, while the cross-linked material collapses through spontaneous cycloreversion upon standing in the dark at ambient temperature. Importantly, the covalent cross-links remain stabilized for as long as visible light is present, thereby retaining the material's structural integrity. This enables their potential use in an array of light-directed applications whereby network properties such as stiffness can be tuned by the mildest trigger of all: darkness.
Cinnamic acid derivatives as inhibitors for chorismatases and isochorismatases
Hubrich, Florian,Mordhorst, Silja,Andexer, Jennifer N.
supporting information, p. 1477 - 1481 (2013/03/14)
Chorismatases and isochorismatases catalyse the hydrolysis of chorismate or isochorismate leading to unsaturated cyclohexenoic acid derivatives. Based on simplification of the physiological substrates, two cinnamic acid-derived compounds, differing in the