194149-75-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 180133-61-3 (4R,5S)-4-methyl-5-methoxy-6-phenyl-2-hexyne 
• 184354-30-1 (3R,4S)-1,1-dibromo-4-methoxy-5-phenyl-3-methyl-pent-1-ene 
• 194149-74-1 [(1R,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 194149-66-1 (E)-(3R,4S)-1-iodo-3-(N-tert-butoxycarbonyl)amino-5-(tert-butyldimethylsiloxy)-4-methyl-pent-1-ene 
• 194149-73-0 (E)-(4S, 5S)-methyl-4-azido-6-(tert-butyldimethylsiloxy)-5-methyl-hex-2-enoate 
• 194149-67-2 (E)-(5R, 6S)-methyl 6-methoxy-7-phenyl-5-methylhept-3-enoate 
• 194149-70-7 (E)-(4S, 5S)-methyl-4-(N-tert-butoxycarbonyl)amino-6-(tert-butyldimethylsiloxy)-5-methyl-hex-2-enoate 
• 194149-68-3 (R)-Azido-[(2R,3S,4R)-3-(dimethyl-phenyl-silanyl)-4-methyl-tetrahydro-furan-2-yl]-acetic acid methyl ester 
• 126399-11-9 (2S,3S,4E)-6-bromo-2-methoxy-3,5-dimethyl-1-phenyl-4-hexene 
• 126399-05-1 (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol 
• 126399-04-0 (2E,4S,5S)-ethyl 5-methoxy-2,4-dimethyl-6-phenylhex-2-enoate 
• 126399-06-2 (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-enyl(triphenyl)phosphonium bromide 
• 238745-93-2 (2S,3S,8S,9S,4E,6E)-3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-1-p-methoxybenzyloxy-4,6-decadiene 

Downstream Products

• 141672-08-4 (-)-motuporin 
• 170872-85-2 dimethyl motuporine hydrate 
• 474085-61-5 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 
• 474085-57-9 C₅₂H₈₅N₅O₁₄Si 
• 134440-92-9 (2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid 

Relevant academic research and scientific papers

Enantioselective synthesis of the protein phosphatase inhibitor (-)-motuporin

A highly convergent asymmetric synthesis of the protein phosphatase inhibitor motuporin 1a is described. Synthesis and coupling of the individual peptide fragments [34 + -35 → 51] followed by macrocyclization afforded the fully protected motuporin precursor 33, which is converted to the natural product by dehydration and ester hydrolysis, Six of the eight stereogenic centers associated with the natural product were introduced using asymmetric crotylsilane bond construction methodology. Our approach features an efficient Pd(0)-catalyzed cross-coupling reaction between a configurationally well-defined vinyl zinc intermediate 22 and an (E)-vinyl iodide 7, which afforded compound 43, resulting in the construction of the trisubstituted (E,E)-diene system of the motuporin side chain. Improved reaction conditions for macrocyclization in the formation of 33 are also detailed.

Total synthesis of motuporin (nodularin-v)

The serine/threonine phosphatase (protein phosphatase 1 and 2A) inhibitors constitute a biologically and structurally interesting class of natural products. Among this class of inhibitors are cyclic pentapeptides (nodularins) and cyclic heptapeptides (mic