1428771-79-2Relevant academic research and scientific papers
Tandem aza-Michael/spiro-ring closure sequence: Access to a versatile scaffold and total synthesis of (±)-coerulescine
G?rmen, Meral,Le Goff, Ronan,Lawson, Ata Martin,Da?ch, Adam,Comesse, Sébastien
, p. 2174 - 2176 (2013/04/24)
The total synthesis of the alkaloid (±)-coerulescine is presented. The key step of this approach is an efficient tandem aza-Michael initiated ring closure (aza-MIRC) process between ethoxymethylene-oxindole and benzyl(2-bromoethyl)carbamate. The potency of the aza-MIRC reaction was first tested onto less challenging Michael acceptors and led in good yields to the corresponding N-Cbz α-alkoxy-β-gem-disubstituted pyrrolidines. The resulting N-acyliminium precursor obtained from ethoxymethylidene-oxindole was efficiently converted in four steps, including 2 deprotections, into the targeted (±)-coerulescine.
