143264-76-0

Upstream product

• 6719-33-1 5,5-dimethoxy-1-oxopentanoic acid 
• 143264-72-6 N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine 
• 143264-75-9 (2R,5R)-2-But-3-enyl-5-methoxy-1-(toluene-4-sulfonyl)-pyrrolidine 
• 143264-74-8 [(2S,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol 
• 132974-84-6 (-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 143264-73-7 N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-methoxypyrrolidine 

Downstream Products

• 64314-16-5 (+)-anatoxin-a hydrochloride 
• 64285-06-9 anatoxin-a 
• 143264-77-1 (-)-N-tosylanatoxin-a 

Relevant academic research and scientific papers

Concise Synthesis of (+)-[13C4]-Anatoxin-a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

An asymmetric total synthesis of [13C4]-anatoxin-a ([13C4]-1) has been developed from commercially available ethyl [13C4]-acetoacetate ([13C4]-15). The unique requirements associated with isotope incorporation inspired a new, robust, and highly scalable route, providing access to 0.110 g of this internal standard for use in the detection and precise quantification of anatoxin-a in freshwater. A highlight of the synthesis is a method that leverages a cyclic iminium ion racemization to achieve dynamic kinetic resolution in an enantioselective Morita–Baylis–Hillman (MBH) cyclization.

A short and enantioselective synthesis of (+)-Anatoxin-a

A short and enantioselective total synthesis of the neurotoxic alkaloid (+)-Anatoxin-a (1) from the L-pyroglutamic acid derivative 2 is described. The key step involves an intramolecular cyclisation of an N-tosyl iminium ion derived from the corresponding α-methoxy sulfonamide.