134440-91-8

Upstream product

• 134440-97-4 (2R,3S)-2-(tert-butoxycarbonyl)amino-3-methoxycarbonyl-3-methylbutanal 
• 126399-06-2 (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-enyl(triphenyl)phosphonium bromide 
• 180133-64-6 (2S,3R,4E)-3-(tert-butoxycarbonyl)amino-2-methyl-5-iodo-4-pentenoic acid methyl ester 
• 67279-64-5 (E)-(2S,3R)-2-Methoxy-3-methyl-hex-4-enoic acid 
• 126399-05-1 cis/trans-(4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol 
• 134440-96-3 (2S,3R)-N-tert-butoxycarbonyl-2-methyl-3-amino-4-hydroxy methyl butanoate 
• 126399-11-9 cis/trans-(4S,5S)-1-bromo-5-methoxy-2,4-dimethyl-6-phenylhex-2-ene 
• 126399-03-9 cis/trans-(4S,5S)-ethyl-5-methoxy-2,4-dimethyl-6-phenylhex-2-enoate 
• 180133-63-5 (4S,5S,2E)-2-iodo-5-methoxy-4-methyl-6-phenyl-2-hexene 
• 126399-06-2 ((E)-(4S,5S)-5-Methoxy-2,4-dimethyl-6-phenyl-hex-2-enyl)-triphenyl-phosphonium; bromide 
• 223923-39-5 (2R,3R)-2-(N-Boc-amino)-3-methylhex-4-enol tert-butyldimethylsilyl ether 
• 82706-51-2 E-(2S,3R)-(N-Boc-amino)-3-methyl-4-hexenoic acid 
• 137172-56-6 ((3R,4S)-4-Methyl-5-oxo-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester 
• 177019-70-4 (E)-(2S,3R)-2-Methoxy-3-methyl-hex-4-enoic acid methyl ester 

Downstream Products

• 141672-08-4 (-)-motuporin 
• 223923-83-9 Dimethylmotuporin 
• 223923-73-7 (4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester 
• 223923-68-0 (2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid 
• 223923-64-6 (2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid 2-trimethylsilanyl-ethyl ester 
• 223923-94-2 (2S,5R,6S,9R,12S,13S,16R)-9-Isopropyl-12-((1E,3E)-(5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-hepta-1,3-dienyl)-1,2,6,13-tetramethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaaza-cyclononadecane-5,16-dicarboxylic acid dimethyl ester 
• 223923-93-1 (2S,5R,6S,9S,12S,13S,16R)-9-Isopropyl-12-((1E,3E)-(5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-hepta-1,3-dienyl)-1,2,6,13-tetramethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaaza-cyclononadecane-5,16-dicarboxylic acid dimethyl ester 
• 223923-92-0 3-(1-allyloxycarbonyl-2-methyl-propylcarbamoyl)-2-(2-{[4-(3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-propionylamino)-butyric acid methyl ester 
• 223924-04-7 2-[3-(2-{[4-(3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyrylamino)-3-methoxycarbonyl-2-methyl-propionylamino]-3-methyl-butyric acid 
• 223923-79-3 3-(1-allyloxycarbonyl-2-methyl-propylcarbamoyl)-2-(2-{[4-(3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-but-2-enoylamino)-butyric acid methyl ester 
• 223924-03-6 3-(1-allyloxycarbonyl-2-methyl-propylcarbamoyl)-2-(2-{[4-(3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyrylamino)-butyric acid methyl ester 
• 96180-79-9 Microcystin-LA 

Relevant academic research and scientific papers

Total synthesis of motuporin and 5-[L-Ala]-motuporin

Total synthesis of the cyclic peptide hepatotoxin motuporin is described, including an efficient synthesis of the constituent amino acid Adda. Three strategies to motuporin are outlined with their relative strengths and weaknesses. Cyclization of the linear peptide precursor was found to proceed moderately well for peptides containing the N- methyldehydrobutyrine residue masked as a threonine, but significant C- terminal epimerization occurred in the presence of the dehydroamino acid. Replacement of the N-methyldehydrobutyrine residue by L-alanine was explored to assess the contribution of this dehydroamino acid to the biochemical activity of motuporin. Some epimerization also was observed during cyclization of the alanine-containing peptide. Synthetic motuporin and both isomers of 5-[L-Ala]-motuporin inhibit the activity of protein phosphatase-1 (PP1) in rat adipocyte lysates with comparable IC50 values. These results indicate that the N-methyldehydrobutyrine residue is not essential for PP1 inhibition.

Stereoconvergent synthesis of (2S,3S,8S,9S,4E,6E)-N-Boc-ADDA starting from (S)-serine and (S)-phenyllactic acid

The important naturally occurring β-amino acid N-Boc-ADDA is prepared following a disconnection of the C-C bond between the two E,E double bonds. The stereochemistry of the two synthons was controlled using the alkylation of chiral bromoallenes derived fr

Total synthesis of the serine-threonine phosphatase inhibitor microcystin-LA

Reversible protein phosphorylation, which is mediated by kinases and phosphatases, is a major control element of the cell. There is a diverse group of toxic natural products that inhibit certain phosphatases, thereby disrupting normal biochemical pathways

A new stereoselective route to (2S, 3S, 8S, 9S, 4E, 6E)-3-amino-9-methoxy-2, 6, 8-trimethyl-10-phenyldeca-4, 6-dienoic acid (Adda)

N-Boc-Adda has been prepared in 15 steps and 9% overall yield from the readily available alcohol, 3-pentyne-2-ol, employing a route that includes two Claisen rearrangements.

Stereocontrolled Synthesis of (2S,3S,8S,9S,4E,6E)-3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic Acid (Adda), the Amino Acid Characteristic of Microcystins and Nodularin

(4R,5S)-4-Methyl-5-phenyloxazolidin-2-one has been used as a chiral template to construct the 8S and 9S chiral centres of (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (Adda), the 2S and 3S centres being derived from D-asp