1192217-76-7Relevant articles and documents
Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
Steeds, Hannah G.,Knowles, Jonathan P.,Yu, Wai L.,Richardson, Jeffery,Cooper, Katie G.,Booker-Milburn, Kevin I.
, p. 14330 - 14334 (2020/10/12)
A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.
Discovery of N-arylpyrroles as agonists of GPR120 for the treatment of type II diabetes
Winters, Michael P.,Sui, Zhihua,Wall, Mark,Wang, Yuanping,Gunnet, Joseph,Leonard, James,Hua, Hong,Yan, Wen,Suckow, Arthur,Bell, Austin,Clapper, Wilmelenne,Jenkinson, Celia,Haug, Peter,Koudriakova, Tatiana,Huebert, Norman,Murray, William V.
, p. 841 - 846 (2018/02/21)
The discovery of a novel series of N-arylpyrroles as agonists of GPR120 (FFAR4) is discussed. One lead compound is a potent GPR120 agonist, has good selectivity for related receptor GPR40 (FFAR1), has acceptable PK properties, and is active in 2 models of Type 2 Diabetes in mice.
Optional synthesis of 2- OR 5-substituted 3-bromopyrroles via bromine-lithium exchange of N-benzenesulfonyl-2,4-dibromopyrrole
Fukuda, Tsutomu,Iwao, Masatomo
, p. 1261 - 1273 (2013/08/23)
The regioselective bromine-lithium exchange of N-benzenesulfonyl-2,4- dibromopyrrole (6) with n-BuLi followed by treatment with various electrophiles gave 5-substituted 3-bromopyrroles (5) in excellent yields. In contrast, the sequential treatment of 6 wi
Directed lithiation of N -benzenesulfonyl-3-bromopyrrole. Electrophile-controlled regioselective functionalization via dynamic equilibrium between C-2 and C-5 lithio species
Fukuda, Tsutomu,Ohta, Takeshi,Sudo, Ei-Ichi,Iwao, Masatomo
supporting information; experimental part, p. 2734 - 2737 (2010/08/19)
(Figure presented) Directed lithiation of N-benzenesulfonyl-3-bromopyrrole (1) with LDA in THF at -78 °C generated C-2 lithio species 3 selectively. Reactions of 3 with reactive electrophiles produced the corresponding 2-functionalized pyrroles 4. On the
Design and synthesis of lamellarin D analogues targeting topoisomerase I
Ohta, Takeshi,Fukuda, Tsutomu,Ishibashi, Fumito,Iwao, Masatomo
experimental part, p. 8143 - 8153 (2010/02/17)
(Chemical Equation Presented) A general synthetic route to rationally designed lamellarinDanalogues, 1-dearyllamellarinD(1) and 1-substituted 1-dearyllamellarin D (2), has been developed. The key pentacyclic intermediate 22 was prepared by palladium-catalyzed direct arylation of 12, which in turn was synthesized via C-2-selective lithiation of 15 followed by palladium-catalyzed cross-coupling as the key reactions. Compound 22 was converted to a wide range of C-1-substituted analogues 2 via regioselective electrophilic substitution and palladium-catalyzed cross-coupling reactions.
