43121-71-7Relevant academic research and scientific papers
Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]
Akaev, Andrey A.,Bezzubov, Stanislav I.,Desyatkin, Victor G.,Vorobyeva, Nataliya S.,Majouga, Alexander G.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
, p. 3340 - 3356 (2019/03/11)
A novel stereocontrolled assembly of spiro[oxindole-3,2′-pyrrolidines] via [3+2]-cycloaddition of donor-acceptor cyclopropanes to electron-poor ketimines, iminooxindoles, was developed. The method allows for efficient employment of common readily available donor-acceptor cyclopropanes, functionalized with ester, keto, nitro, cyano etc. groups, and N-unprotected iminooxindoles. The stereospecificity of the initial SN2-like imine attack on a cyclopropane molecule together with a high diastereoselectivity of further C-C bond formation facilitate a rapid access to spiro[oxindole-3,2′-pyrrolidines] in their optically active forms. Preliminary in vitro testing of the synthesized compounds against LNCaP (p53+) and PC-3 (p53-) cells revealed good antiproliferative activities and p53-selectivity indices for several compounds that are intriguing in terms of their further investigation as inhibitors of MDM2-p53 interaction.
Model studies on total synthesis of the chartellines, spirocyclic β-lactam alkaloids from a marine bryozoan
Lin, Xichen,Weinreb, Steven M.
, p. 2631 - 2633 (2007/10/03)
A chartelline alkaloid model system containing a spirocyclic β-lactam moiety and α,β-unsaturated imine has been constructed from isatin using a Staudinger imine-ketene cycloaddition and an addition to an N-activated γ-lactam as key steps.
