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.
Chen, Karen Y.,Lacharity, Jacob J.,Mailyan, Artur K.,Zakarian, Armen
supporting information
p. 11364 - 11368
(2020/05/18)
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
Addante-Moya, Luis G.,Agulló, Consuelo,Qui?ones-Reyes, Guillermo,Mercader, Josep V.,Abad-Fuentes, Antonio,Abad-Somovilla, Antonio
p. 5022 - 5031
(2018/05/04)
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
Roe, Stephen J.,Hughes, David L.,Aggarwal, Pooja,Stockman, Robert A.
experimental part
p. 3775 - 3784
(2010/03/30)
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
Roe, Stephen J.,Stockman, Robert A.
supporting information; experimental part
p. 3432 - 3434
(2009/02/05)
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
Huby, Nicholas J. S.,Kinsman, Richard G.,Lathbury, David,Vernon, Peter G.,Gallagher, Timothy
p. 145 - 155
(2007/10/02)
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.
Tufariello,Meckler,Pushpananda,Senaratne
p. 3447 - 3453
(2007/10/02)
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