199103-41-8Relevant academic research and scientific papers
Total synthesis of (+)-gelsedine
Beyersbergen Van Henegouwen, Winfred G.,Fieseler, Rutger M.,Rutjes, Floris P. J. T.,Hiemstra, Henk
, p. 2214 - 2217 (1999)
A novel iodide-promoted, allene-terminated cyclization of an N- acyliminium ion, a stereoselective Heck spirocyclization, and a chemoselective demethylation at the nitrogen atom of an oxindole are the key transformations in the first total synthesis of th
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.
