105174-63-8Relevant articles and documents
Investigation of dopamine analogues: Synthesis, mechanistic understanding, and structure-property relationship
Hu, Huamin,Dyke, Jason Christopher,Bowman, Brett Allen,Ko, Ching-Chang,You, Wei
, p. 9873 - 9882 (2016/10/07)
Dopamine, perhaps the simplest molecule that covalently links catechol and amine, together with its derivatives, has shown impressive adhesive and coating properties with its polymers. However, the scope of the molecules is rather limited, and the polymer
Enantioselective synthesis of quinolizidines and indolizidines via a catalytic asymmetric hydrogenation cascade
Rueping, Magnus,Hubener, Lukas
supporting information; experimental part, p. 1243 - 1246 (2011/07/31)
A catalytic enantioselective synthesis of a new class of quinolizidines and indolizidines is presented. An asymmetric Bronsted acid catalyzed hydrogenation cascade as well as a sequential Bronsted acid/metal catalyzed hydrogenation protocol of 2-substituted quinolines yields benzofused quinolizidines and indolizidines in good yields with high diastereo- and enantioselectivities. Georg Thieme Verlag Stuttgart - New York.
Application of furanyl carbamate cycloadditions toward the synthesis of hexahydroindolinone alkaloids
Padwa,Brodney,Dimitroff,Liu,Wu
, p. 3119 - 3128 (2007/10/03)
A convenient synthesis of various substituted hexahydroindolinones has been achieved by an intramolecular Diels-Alder cycloaddition reaction (IMDAF) of furanyl carbamates bearing tethered alkenyl groups. The initially formed [4 + 2]-cycloadduct undergoes nitrogen-assisted ring opening followed by deprotonation of the resulting zwitterion to give the rearranged ketone. The stereochemical outcome of the IMDAF cycloaddition has the sidearm of the tethered alkenyl group oriented syn with respect to the oxygen bridge. A synthetic route to (±)-mesembrane and (±)-crinane was accomplished using this methodology. It was possible to carry out a stereoselective reduction of the initially formed hexahydroindolinone ring to produce the cis-3a-aryl-hydroindole skeleton. A related [4 + 2]-cycloaddition/rearrangement sequence was also used for a formal synthesis of the Chinese ornamental orchid (±)-dendrobine. The tricyclic alkaloid core was formed stereoselectivity from the thermolysis of N-[(2-methyl-2-cyclopentenyl)methyl]-N-(4-isopropyl-furan-2-yl)carbamic acid tert-butyl ester. Kende's advanced intermediate 33 was prepared in seven additional steps by standard transformations, thereby completing a formal synthesis of (±)-dendrobine.