199103-45-2

Upstream product

• 106-96-7 propargyl bromide 
• 188295-12-7 (S)-1-Benzyl-5-ethoxy-4-hydroxy-pyrrolidin-2-one 
• 129823-21-8 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 

Downstream Products

• 199103-44-1 1-benzyl-5-ethoxy-4-hydroxy-3-(buta-2,3-dienyl)-2-pyrrolidinone 
• 199103-51-0 (1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one 
• 199103-49-6 (1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(hydroxymethylene)-7-azabicyclo[4.2.1]nonane-8-one 
• 199103-47-4 (1S,6R)-7-benzyl-4,4-(ethylenedioxy)-7-azabicyclo[4.2.1]nonane-8,9-dione 
• 199103-46-3 (1S,6R,9S)-7-benzyl-4,4-(ethylenedioxy)-9-hydroxy-7-azabicyclo[4.2.1]nonane-8-one 
• 199103-48-5 (1S,6R)-7-benzyl-4,4-(ethylenedioxy)-9-methylene-7-azabicyclo[4.2.1]nonane-8-one 
• 199103-41-8 (1S,6R,9S)-7-benzyl-9-hydroxy-7-azabicyclo[4.2.1]nonane-4,8-dione 

Relevant academic research and scientific papers

Studies toward the Total Synthesis of the Oxindole Alkaloid Gelsedine: An Efficient Allene-Terminated N-Acyliminium Ion Cyclization

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.