112463-92-0

Upstream product

• 113089-15-9 (S)-2-methoxycarbonylamino-3-(4-methoxyphenyl)-propionic acid methyl ester 
• 114495-36-2 (R)-2-Methoxycarbonylamino-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 60-18-4 L-tyrosine 
• 361520-05-0 (S)-2-[(methoxycarbonyl)amino]-3-(4-methoxyphenyl) propan-1-ol 
• 338386-45-1 (S)-3-(4-hydroxyphenyl)-2-[(methoxycarbonyl)amino] propionic acid 

Downstream Products

• 112463-93-1 (S)-2,2-Dichloro-3-hydroxy-4-methoxycarbonylamino-5-(4-methoxy-phenyl)-pentanoic acid methyl ester 
• 112463-93-1 (R)-2,2-Dichloro-3-hydroxy-4-methoxycarbonylamino-5-(4-methoxy-phenyl)-pentanoic acid methyl ester 
• 112464-01-4 Acetic acid (3S,4R,5R)-4-hydroxy-5-(4-methoxy-benzyl)-2-oxo-pyrrolidin-3-yl ester 
• 112463-97-5 (1R,4R,5R)-4-(4-Methoxy-benzyl)-6-oxa-3-aza-bicyclo[3.1.0]hexan-2-one 
• 112487-80-6 Acetic acid (3S,4R,5R)-4-methanesulfonyloxy-5-(4-methoxy-benzyl)-2-oxo-pyrrolidin-3-yl ester 
• 112463-94-2 (R)-3,3-Dichloro-4-hydroxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 112463-95-3 (R)-3-Chloro-4-hydroxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 27958-06-1 (2R,3S,4S)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 113158-90-0 (4S,5S)-3,3-Dichloro-4-hydroxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 113158-91-1 (4R,5S)-3,3-Dichloro-4-hydroxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one 

Relevant academic research and scientific papers

Chemical and Genetic Studies on the Formation of Pyrrolones During the Biosynthesis of Cytochalasans

A key step during the biosynthesis of cytochalasans is a proposed Knoevenagel condensation to form the pyrrolone core, enabling the subsequent 4+2 cycloaddition reaction that results in the characteristic octahydroisoindolone motif of all cytochalasans. In this work, we investigate the role of the highly conserved α,β-hydrolase enzymes PyiE and ORFZ during the biosynthesis of pyrichalasin H and the ACE1 metabolite, respectively, using gene knockout and complementation techniques. Using synthetic aldehyde models we demonstrate that the Knoevenagel condensation proceeds spontaneously but results in the 1,3-dihydro-2H-pyrrol-2-one tautomer, rather than the required 1,5-dihydro-2H-pyrrol-2-one tautomer. Taken together our results suggest that the α,β-hydrolase enzymes are essential for first ring cyclisation, but the precise nature of the intermediates remains to be determined.

A new Stereoselective Method of Synthesis of Pyrrolizidines and Indolizidines

The addition of electrogenerated dichloro(methoxycarbonyl)methyl anions to some N-(methoxycarbonyl)-α-amino aldehydes prepared from α-amino acids was found to show about 100percent diastereoselectivity.Some alkaloid type compounds containing pyrrolizidine and indolizidine skeletons were synthesized from the adducts.

Total Synthesis of (-)-Anisomycin

Antibiotic (-)-anisomycin was synthesized starting from D-tyrosine using the addition of electrogenerated dichloro-(methoxycarbonyl)methyl anion to aldehyde 2 as a key reaction.