143264-77-1

Upstream product

• 143264-76-0 (E)-6-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-hex-3-en-2-one 
• 916152-70-0 [(2S,5S)-5-But-3-enyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol 
• 916152-63-1 (2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine 
• 916152-69-7 3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde 
• 143264-79-3 (2R,5R)-2-Methoxy-1-(toluene-4-sulfonyl)-5-((E)-5-trimethylsilanyl-pent-4-enyl)-pyrrolidine 
• 143264-72-6 N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine 
• 143264-80-6 (1R,6R)-9-(Toluene-4-sulfonyl)-2-vinyl-9-aza-bicyclo[4.2.1]nonane 
• 143264-75-9 (2R,5R)-2-But-3-enyl-5-methoxy-1-(toluene-4-sulfonyl)-pyrrolidine 
• 132974-84-6 (-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one 
• 716336-79-7 3-((2S,5R)-2-(tert-butyldiphenylsilyloxymethyl)-1-p-toluenesulfonylpyrrolidin-5-yl)-propan-1-ol 
• 716336-80-0 (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine 

Downstream Products

• 64285-06-9 anatoxin-a 
• 64314-16-5 (+)-anatoxin-a hydrochloride 

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.

Further studies on enantioselective synthesis of (+)-anatoxin-a using enyne metathesis: unexpected inversion of chirality via a skeletal rearrangement of 9-azabicyclo[4.2.1]nonene derivative

The formal total synthesis of (+)-anatoxin-a was accomplished using enyne metathesis as a key step. It is very interesting that (+)-anatoxin-a was synthesized from (S)-pyroglutamic acid via an unusual inversion of chirality, which is rationalized in terms

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.