61322-97-2Relevant academic research and scientific papers
Highly Reactive and Tracelessly Cleavable Cysteine-Specific Modification of Proteins via 4-Substituted Cyclopentenone
Yu, Jian,Yang, Xiaoyue,Sun, Yang,Yin, Zheng
, p. 11598 - 11602 (2018/09/10)
A rapid and cysteine-specific modification of proteins using 4-substituted cyclopentenone via a Michael addition tandem elimination reaction was developed. Compared to the classical method, this reaction featured fast kinetics with a stable product. More importantly, this conjugation could be tracelessly removed by exchange with a Michael addition donor. The conjugation and regeneration process not only exhibited little change to the structures or conformations of the proteins but also exhibited little disturbance to their biological functions, such as their enzymatic activities.
Total synthesis, relay synthesis, and structural confirmation of the C18-norditerpenoid alkaloid neofinaconitine
Shi, Yuan,Wilmot, Jeremy T.,Nordstrom, Lars Ulrik,Tan, Derek S.,Gin, David Y.
supporting information, p. 14313 - 14320 (2013/10/21)
The first total synthesis of the C18-norditerpenoid aconitine alkaloid neofinaconitine and relay syntheses of neofinaconitine and 9-deoxylappaconitine from condelphine are reported. A modular, convergent synthetic approach involves initial Diels-Alder cycloaddition between two unstable components, cyclopropene 10 and cyclopentadiene 11. A second Diels-Alder reaction features the first use of an azepinone dienophile (8), with high diastereofacial selectivity achieved via rational design of siloxydiene component 36 with a sterically demanding bromine substituent. Subsequent Mannich-type N-acyliminium and radical cyclizations provide complete hexacyclic skeleton 33 of the aconitine alkaloids. Key endgame transformations include the installation of the C8-hydroxyl group via conjugate addition of water to a putative strained bridghead enone intermediate 45 and one-carbon oxidative truncation of the C4 side chain to afford racemic neofinaconitine. Complete structural confirmation was provided by a concise relay synthesis of (+)-neofinaconitine and (+)-9-deoxylappaconitine from condelphine, with X-ray crystallographic analysis of the former clarifying the NMR spectral discrepancy between neofinaconitine and delphicrispuline, which were previously assigned identical structures.
A Facile, Efficient Synthesis of 2-substituted-4-Hydroxy-2-cyclopenten-1-ones
Baraldi, P. G.,Pollini, G. P.,Simoni, D.,Zanirato, V.,Barco, A.,Benetti, S.
, p. 781 - 782 (2007/10/02)
A simple procedure for the transformation of 2-substituted 4-bromo-2-cyclopenten-1-ones into the title compounds as well as into the corresponding 4-methoxy derivatives is described.
