225779-62-4Relevant academic research and scientific papers
Concise Synthesis of (+)-[13C4]-Anatoxin-a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion
Chen, Karen Y.,Lacharity, Jacob J.,Mailyan, Artur K.,Zakarian, Armen
supporting information, p. 11364 - 11368 (2020/05/18)
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
Tomita, Tomohiro,Kita, Yoichi,Kitamura, Tsuyoshi,Sato, Yoshihiro,Mori, Miwako
, p. 10518 - 10527 (2007/10/03)
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
Synthesis of (+)-anatoxin-a using enyne metathesis
Mori, Miwako,Tomita, Tomohiro,Kita, Yoichi,Kitamura, Tsuyoshi
, p. 4397 - 4399 (2007/10/03)
Synthesis of N-tosylanatoxin-a was achieved by metathesis of enyne in cis-substituents on a pyrrolidine derivative. Metathesis reactions of enyne having terminal alkyne using various ruthenium-carbene complexes did not give a good results. However, when t
Asymmetric synthesis of (-)-anatoxin-a via an asymmetric cyclization using a new ligand for Pd-catalyzed alkylations
Trost, Barry M.,Oslob, Johan D.
, p. 3057 - 3064 (2007/10/03)
Palladium-catalyzed asymmetric allylic alkylations have been explored in the context of medium-sized ring substrates, intramolecular vs intermolecular processes involving attack on a formally meso π-allyl intermediate in the desymmetrization, and the pres
