174905-91-0

Upstream product

• 174905-84-1 N,N-diethyl-3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>benzenemethanamine 
• 174905-82-9 N,N-diethyl-3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>benzamide 
• 824-94-2 p-methoxybenzyl chloride 
• 38228-27-2 N,N-diethyl-3,5-dimethoxybenzamide 
• 174905-86-3 1-(chloromethyl)-3,5-dimethoxy-2-{[(4-methoxyphenyl)methyl]thio}benzene 
• 174905-89-6 (2R-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine 

Downstream Products

• 221333-40-0 (5S,10aS)-9-<<5-<(2S-trans)-2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)pyrazin-5-yl>methyl-1-methyl-1H-imidazol-4-yl>thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 221333-46-6 (5S,10aS)-9-<<5-<(2S-cis)-2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)pyrazin-5-yl>methyl-1-methyl-1H-imidazol-4-yl>thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 221332-83-8 (5S,10aS)-5-<<6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-3(3H)-oxo-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-9-yl>thio>-3-methyl-D-histidine methyl ester 
• 221333-26-2 (5S,10aS)-6,8-dimethoxy-9-<(5-hydroxymethyl-1-methyl-1H-imidazol-4-yl)thio>-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 221333-10-4 (S)-N-<2-(acetyloxy)-1-<<3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>ethyl>-4-methoxybenzeneacetamide 
• 221333-12-6 (1S,3S)-3-acetyloxymethyl-6,8-dimethoxy-1-<(4-methoxyphenyl)methyl>-5-<<(4-methoxyphenyl)methyl>thio>-1,2,3,4-tetrahydroisoquinoline 
• 221333-22-8 (5S,10aS)-6,8-dimethoxy-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 221333-15-9 (5S,10aS)-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-9-<<(4-methoxyphenyl)methyl>thio>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 221332-96-3 (1S,3S)-6,8-dimethoxy-1-<(4-methoxyphenyl)methyl>-5-<<(4-methoxyphenyl)methyl>thio>-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester 
• 221333-02-4 (1S,3S)-6,8-dimethoxy-3-hydroxymethyl-1-<(4-methoxyphenyl)methyl>-5-<<(4-methoxyphenyl)methyl>thio>-1,2,3,4-tetrahydroisoquinoline 
• 221333-06-8 (S)-N-<2-<3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>phenyl>-1-(hydroxymethyl)ethyl>-4-methoxybenzeneacetamide 
• 221333-19-3 (5S,10aS)-6,8-dimethoxy-9-mercapto-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 221332-90-7 N-<(4-methoxyphenyl)acetyl>-3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-L-phenylalanine methyl ester 

Relevant academic research and scientific papers

Synthetic studies on the starfish alkaloid imbricatine. A chiral synthesis of tri-O-methylimbricatine

A detailed account is given of the chiral synthesis of tri-O- methylimbricatine (3), the triO-methyl derivative of the structurally unique benzyltetrahydroisoquinoline alkaloid imbricatine (2) isolated from the starfish Dermasterias imbricata. The route begins with the asymmetric synthesis of the sulfur-containing D-phenylalanine derivative (R)-11a and includes its conversion into the cis-benzyltetrahydroisoquinoline moiety 26a possessing the thiol group and construction of the 5-arylthio-3-methyl-L- histidine portion. The correctness of the structure and absolute configuration proposed for imbricatine has been unequivocally confirmed as a result of the present synthesis.

Syntheses of 1-phenylalanine derivatives containing a sulfur substituent at the 2-position

A full account is given of the chiral syntheses of sulfur-containing L-phenylalanine derivatives (8b,c), selected as key intermediates for the synthesis of models for the starfish alkaloid imbricatine (7), via a 5-step route starting from N,N-diethyl-3,5-dimethoxybenzamide (9). The key steps involve introduction of a sulfur substituent into 9 at the 2-position and construction of the chiral α-amino acid moiety in the chlorides (12b,c) by the "bis-lactim ether" method.