199103-42-9Relevant academic research and scientific papers
Studies toward the Total Synthesis of the Oxindole Alkaloid Gelsedine: An Efficient Allene-Terminated N-Acyliminium Ion Cyclization
Beyersbergen van Henegouwen, Winfred G.,Hiemstra, Henk
, p. 8862 - 8867 (2007/10/03)
This paper reports the synthesis of the advanced intermediate 26 in a projected synthesis of enantiopure ent-gelsedine (5). The route starts from (S)-malic acid and features the creation of four new stereocenters with complete control of stereochemistry. The key step is a novel allene-terminated N-acyliminium ion cyclization that leads to the required 7-azabicyclo[4.2.1]nonane-4,8-dione skeleton. Additional functionalities including the C-8 ethyl and the C-9 hydroxymethyl are introduced in an efficient manner.
Regioselective reductions of various 3-aminosuccinimides; application to the synthesis of two heterocyclic systems
Briere, Jean-Francois,Charpentier, Patricia,Dupas, Georges,Queguiner, Guy,Bourguignon, Jean
, p. 2075 - 2086 (2007/10/03)
The synthesis of novel pyrrolo[3,2-c]isoquinolines is investigated starting from 3-aminosuccinimides. Various known routes leading to 3-aminosuccinimides were tested but a new approach via nucleophilic addition of arylalkylamines on maleimide gave better results. The regioselectivity of the reduction of these compounds was shown to depend on the degree of substitution of the concerned 3-aminosuccinimide. The hydroxylactams are formed in-situ, then converted into the ethoxylactams. The latter, after generation of an iminium salt, afforded the target pyrroloisoquinolines and two further derivatives of another new heterocyclic system: the 3,6-methano-2,5-benzodiazocine.
