928209-69-2

Upstream product

• 35396-23-7 2-Amino-2-desoxy-3-O-t-butyl-sn-glycerin 
• 17083-26-0 O-tert-butyl-L-serine methyl ester 
• 928209-67-0 2-bromo-1-(4-tert-butoxymethyl-2,2-dimethyl-oxazolidin-3-yl)-ethanone 
• 928209-80-7 4-tert-butoxymethyl-2,2-dimethyl-oxazolidine 
• 928209-68-1 2-benzenesulfonyl-1-(4-tert-butoxymethyl-2,2-dimethyl-oxazolidin-3-yl)-2-diazo-ethanone 
• 928209-81-8 2-benzenesulfonyl-1-(4-tert-butoxymethyl-2,2-dimethyl-oxazolidin-3-yl)-ethanone 

Downstream Products

• 928209-71-6 4-tert-butoxy-5-hydroxymethyl-pyrrolidin-2-one 
• 154226-60-5 omuralide 

Relevant 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

(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.

Stereogenic evolution of clasto-lactacystin β-lactone from L-serine

Reported herein is a novel synthesis of clasto-lactacystin β-lactone. The γ-lactam core was selectively prepared by an intramolecular C-H insertion to establish the stereocenter, C(6). The ensuing construction of the quaternary C(5) and carbinol C(9) cent