1004306-56-2Relevant academic research and scientific papers
Total syntheses of (-)-α-kainic acid and (+)-α-allokainic acid via stereoselective C-H insertion and efficient 3,4-stereocontrol
Young, Chun Jung,Cheol, Hwan Yoon,Turos, Edward,Kyung, Soo Yoo,Kyung, Woon Jung
, p. 10114 - 10122 (2007)
(Chemical Equation Presented) Reported herein is a novel approach to the total syntheses of (-)-α-kainic acid and (+)-α-allokainic acid, where the stereochemistries on C(2), C(3), and C(4) of the pyrrolidine core were introduced efficiently and selectively. A regio- and stereoselective C-H insertion reaction was utilized to prepare the γ-lactam as an intermediate. A Michael-type cyclization of phenylsulfone with a conjugated acetylenic ketone was developed to prepare the tricyclic ketone as a key intermediate for (-)-α-kainic acid. Subsequently, a stereoselective dephenylsulfonylation was carried out successfully to secure the cis relationship at C(3) and C(4) centers. An unprecedented acetylation on the phenylsulfone, followed by a stereoselective dephenylsulfonylation, secured the trans relationship at C(3) and C(4) centers in (+)-α-allokainic acid.
