64314-16-5

Usage

InChI:InChI=1/C10H15NO.ClH/c1-7(12)9-4-2-3-8-5-6-10(9)11-8;/h4,8,10-11H,2-3,5-6H2,1H3;1H/t8?,10-;/m0./s1

Upstream product

• 92844-76-3 hexahydro-3-hydroxy-2,7-methano-2H-pyrrolo<1,2-b>-<1,2>-oxazin-9-yl methyl ketone 
• 64285-06-9 (+/-)-Anatoxin A 
• 143264-77-1 (-)-N-tosylanatoxin-a 
• 143264-76-0 (E)-6-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-hex-3-en-2-one 
• 895138-29-1 (1R,6R)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one 
• 895138-28-0 (1R,2R,6R)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-ol 
• 90741-53-0 (1R)-2-acetyl-9-(1-tert-butoxycarbonyl)-9-azobicyclo<4.2.1>-2-nonene 
• 19740-90-0 (Z)-9-oxabicyclo[6.1.0]non-4-ene 

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 unified approach to the synthesis of both enantiomers of anatoxin-a and homoanatoxin-a cyanotoxins

Anatoxin-a and homoanatoxin-a are highly neurotoxic compounds produced by cyanobacteria, principally during surface water-blooms (SWBs). Owing to their powerful biological activity and unique structural characteristics, these natural alkaloids have been t

Investigation of a unified strategy for the synthesis of anatoxin analogues: Scope and limitations

Syntheses of the potent neurotoxins and biochemical probes anatoxin-a and homoanatoxin and several analogues by a combined two-directional synthesis-tandem reaction strategy are presented. Key steps include an oxidative desymmetrisation and a tandem Micha

A two-directional approach to the anatoxin alkaloids: Second synthesis of homoanatoxin and efficient synthesis of anatoxin-a

Total syntheses of the potent neurotoxins, environmental hazards, and biochemical probes anatoxin-a and homoanatoxin have been achieved from a common intermediate using a combined two-directional synthesis-tandem reaction strategy which includes key advan

Synthetic and Stereochemical Studies Directed Towards Anatoxin-a

The synthesis and stereocontrolled Ag1-catalysed cyclisation of a series of allenic amino esters 8a-e is described.For compounds 8a-d the cis-2,5-disubstituted pyrrolidine 9 is formed exclusively but the primary amine 8e undergoes cyclisation n

The use of nitrones in the synthesis of anatoxin-a, very fast death factor

The synthesis of anatoxin-a (1) was completed by using the cycloaddition of 1-pyrroline-1-oxide (2) onto dienol (6), a reaction which proceeded with high stereoselectivity, regioselectivity, and site selectivity. The resultant adduct (i.e. 7) was oxidized to a second nitrone (i.e. 8) which undergoes a second closure to afford cycloadduct 9a with regiospecificity. The conversion of 9a into anatoxin-a hydrochloride (1 · HCl) was both direct and efficient.