150674-69-4Relevant academic research and scientific papers
A formal synthesis of (–)-kainic acid by means of SMI2-mediated radical cyclization
Takahashi, Kazunori,Ito, Takumi,Yamada, Wataru,Tsubuki, Masayoshi,Honda, Toshio
, p. 882 - 894 (2018/06/04)
A formal synthesis of (–)-kainic acid (1) starting from the known D-serine derivative 9 has been established in 14 steps. Construction of all the stereogenic centers on the pyrrolidine core of 1 was successfully achieved by application of SmI2-mediated radical cyclization to the α,β-unsaturated ester having an alkyne moiety, followed by hydroxy group directed diastereoselective hydrogenation over Wilkinson’s catalyst.
Substrate stereocontrol in the intramolecular organocatalyzed tsuji-trost reaction: Enantioselective synthesis of allokainates
Vulovic, Bojan,Gruden-Pavlovic, Maja,Matovic, Radomir,Saicic, Radomir N.
supporting information, p. 34 - 37 (2014/01/23)
Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.
Total synthesis of (-)-(α)-kainic acid via a diastereoselective methylenecyclopropane ring expansion
Scott, Mark E.,Lautens, Mark
, p. 3045 - 3047 (2007/10/03)
(Chemical Equation Presented) A concise and enantioselective synthesis of (-)-(α)-kainic acid in 13 steps with an overall yield of 15% is reported. The pyrrolidine kainoid precursor with the required C2/C3 trans stereochemistry was prepared with excellent diastereoselectivity (>20:1) via a Mgl 2-mediated ring expansion of a tertiary methylenecyclopropyl amide. A selective hydroboration was then employed to set the remaining stereochemistry at the C4 position en route to (-)-(α)-kainic acid.
Radical cyclization in heterocycle synthesis. Part 10: A concise synthesis of (-)-kainic acid via sulfanyl radical addition-cyclization-elimination reaction
Miyata, Okiko,Ozawa, Yoshiki,Ninomiya, Ichiya,Naito, Takeaki
, p. 6199 - 6207 (2007/10/03)
Sulfanyl radical addition-cyclization-elimination of diallylamines in the presence of thiophenol and AIBN gave the 2,3,4-trisubstituted pyrrolidine in high yield. This reaction was extended to a radical cyclization using a catalytic amount of thiophenol. A successful application was demonstrated by the asymmetric synthesis of (-)-kainic acid. (C) 2000 Elsevier Science Ltd.
An Enantioselective Synthesis of (-)-α-Kainic Acid via Thiyl Radical Addition-Cyclization-Elimination Reaction
Miyata, Okiko,Ozawa, Yoshiki,Ninomiya, Ichiya,Naito, Takeaki
, p. 275 - 276 (2007/10/03)
An enantioselective synthesis of (-)-α-kainic acid has been achieved via the route involving thiyl radical addition-cyclization-elimination reaction.
A Total Synthesis of (-)-α-Kainic Acid Involving a Pauson-Khand Reaction as the Key Step
Yoo, Sung-eun,Lee, Sang Hee
, p. 6968 - 6972 (2007/10/02)
A synthetic route to (-)-α-kainic acid has been developed based on the Pauson-Khand reaction as a key step for the construction of the bicyclic ring system.In this reaction a built-in oxazolidinone ring serves as a rigid template for good diastereofacial selectivity.
A Total Synthesis of (-)-α-Kainic Acid By the Pauson-Khand Reaction
Yoo, Sung-eun,Lee, Sang-Hee,Jeong, Nakcheol,Cho, Inho
, p. 3435 - 3438 (2007/10/02)
A total synthetic route to (-)-α-kainic acid has been developed based on the Pauson-Khand reaction as a key reaction for the construction of the bicyclo ring system.
