173204-71-2Relevant academic research and scientific papers
Functionalized Polyhydroquinolines from Amino Acids Using a Key One-Pot Cyclization Cascade and Application to the Synthesis of (±)-Δ7-Mesembrenone
Bélanger, Guillaume,Gallagher-Duval, Shawn,Lapointe, Vincent
supporting information, p. 8606 - 8611 (2021/11/17)
Substituted polyhydroquinolines are ubiquitous skeletal cores found in drugs and bioactive natural products. As a new route to access this motif, we successfully developed a one-pot cyclization cascade with high chemocontrol and diastereoselectivity. The sequence generates two cycles, three carbon-carbon bonds, and an all-carbon quaternary center in a highly convergent process. Functionalized polyhydroquinolines and congeners can be accessed from commercially available amino acids. This versatile and robust strategy was applied to the synthesis of (±)-Δ7-mesembrenone.
Design and synthesis of fused tetrahydroisoquinoline-iminoimidazolines
Moas-Héloire, Valeria,Renault, Nicolas,Batalha, Vania,Arias, Angela Rincon,Marchivie, Mathieu,Yous, Said,Deguine, Noémie,Buée, Luc,Chavatte, Philippe,Blum, David,Lopes, Luisa,Melnyk, Patricia,Agouridas, Laurence
, p. 15 - 25 (2015/11/23)
In the aim of identifying new privileged structures, we describe the 5-steps synthesis of cyclic guanidine compounds "tetrahydroisoquinoline-iminoimidazolinesg" derived from tetrahydroisoquinoline-hydantoin core. In order to evaluate this new minimal structure and the impact of replacing a carbonyle by a guanidine moiety, their affinity towards adenosine receptor A2A was evaluated and compared to those of tetrahydroisoquinoline-hydantoin compounds.
A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization
Palomo, Claudio,Oiarbide, Mikel,Garcia, Jesus M.,Gonzalez, Alberto,Pazos, Raquel,Odriozola, Jose M.,Banuelos, Patricia,Tello, Monica,Linden, Anthony
, p. 4126 - 4134 (2007/10/03)
A practical total synthesis of hapalosin, a compound with multidrug resistance-reversing activity, has been carried out using an unprecedented macrolactonization strategy. One of the features of the new approach is the straightforward and fully stereocont
Synthesis and conformational analysis of the multidrug resistance-reversing agent hapalosin and its non-N-methyl analog
Dinh, Tam Q.,Du, Xiaohui,Armstrong, Robert W.
, p. 6606 - 6616 (2007/10/03)
Hapalosin was initially synthesized by macrolactonization, and a second synthesis was achieved by cycloamidation. In both syntheses, three of the five stereocenters in hapalosin were established by two Brown allylboration reactions. The synthesis of the non-N-Me analog of hapalosin involved chelation-controlled reduction of a γ-amino-β-keto ester and cycloamidation. In CDCl3 at 25°C, synthetic hapalosin exists as a 2.3:1 mixture of conformers, while its non-N-Me analog exists only as a single conformer. 1H,1H-NOESY and computation reveal that the configuration of the amide bond is responsible for the conformations of the two compounds. The major conformer of hapalosin is found to be an s-cis amide, the minor conformer an s-trans amide, and the non-N-Me analog an s-trans amide. Applying distance constraints to protons that exhibit NOESY correlations, computation shows that the major conformer of hapalosin and the non-N-Me analog have very different conformations. By contrast, the minor conformer of hapalosin and the non-N-Me analog have very similar conformations.
