119717-37-2

Upstream product

• 161925-59-3 jaspamide Z₁ 
• 112896-85-2 (R)-3-((R)-3-(2-Bromo-1H-indol-3-yl)-2-{[(S)-2-((E)-(2S,6R,8S)-8-methoxymethoxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester 
• 943858-43-3 C₄₅H₆₅N₄O₆SiBr 
• 69651-48-5 N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine 
• 32462-30-9 (S)-hydroxyphenylglycine 
• 112896-92-1 N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester 
• 112896-87-4 methyl (R)-3-<1-(tert-butyldimethylsilyl)indol-3-yl>-2-(N-tert-butoxycarbonyl-N-methylamino)propanoate 
• 112896-91-0 (S)-N-tert-butoxycarbonyl-4-tert-butyldimethylsilyloxy-α-diazoacetylbenzylamine 
• 112896-83-0 N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester 
• 112896-94-3 N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester 
• 161925-49-1 (2S,4E,6S,8S)-8-benzoyloxy-2,4,6-trimethylnon-4-en-1-ol 
• 161925-45-7 methyl (R)-3-amino-3-<4-(tert-butyldimethylsiloxy)phenyl>propanoate 
• 161925-50-4 (2S,4E,6S,8S)-8-benzoyloxy-2,4,6-trimethylnon-4-en-1-al 
• 4397-53-9 p-benzyloxybenzaldehyde 

Downstream Products

• 102396-25-8 Acetic acid 4-[(E)-7-(2-bromo-1H-indol-3-ylmethyl)-8,10,13,15,17,19-hexamethyl-2,6,9,12-tetraoxo-1-oxa-5,8,11-triaza-cyclononadec-15-en-4-yl]-phenyl ester 
• 103848-63-1 (E)-8-Hydroxy-2,4,6-trimethyl-non-4-enoic acid [1-({2-(2-bromo-1H-indol-3-yl)-1-[3-hydroxy-1-(4-hydroxy-phenyl)-propylcarbamoyl]-ethyl}-methyl-carbamoyl)-ethyl]-amide 
• 161925-59-3 jaspamide Z₁ 

Relevant academic research and scientific papers

Synthesis and structure-activity correlation of natural-product inspired cyclodepsipeptides stabilizing F-actin

The fundamental role played by actin In the regulation of eukaryotic cell maintenance and motility renders it a primary target for small-molecule intervention. in this arena, a class of potent cytotoxic cyclodepsipeptide natural products has emerged over the last quarter-century to stimulate the fields of biology and chemistry with their unique actin-stabilizing properties and complex peptide-polyketide hybrid structures. Despite considerable research effort, a structural basis for the activity of these secondary metabolites remains elusive, not least for the lack of high-resolution structural data and a reliable synthetic route to diverse compound libraries. in response to this, an efficient solid-phase approach has been developed and successfully applied to the total synthesis of Jasplakinolide and chondramide C and diverse analogues. The key macrocylization step was realized using ruthenium-catalyzed ring-closing metathesis (RCM) that in the course of a library synthesis produced discernible trends in metathesis reactivity and E/Z-selectivity, After optimization, the RCM step could be operated under mild conditions, a result that promises to facilitate the synthesis of more extensive analogue libraries for structure-function studies. The growth inhibitory effects of the synthesized compounds were quantified and structure-activity correlations established which appear to be in good alignment with relevant biological data from natural products. in this way a number of potent unnatural and simplified analogues have been found. Furthermore, potentially important stereochemical and structural components of a common pharmacophore have been identified and rationalized using molecular modeling. These data will guide in-depth mode-of-action studies, especially into the relationship between the cytotoxicity of these compounds and their actin-perturbing properties, and should inform the future design of simplified and functionalized actln stabilizers as well.

Solid-phase based total synthesis of Jasplakinolide by ring-closing metathesis

The study of classical ring-closing metathesis and relay ring-closing metathesis in a total synthesis of Jasplakinolide and its desbromo analog is described.

Enantioselective total synthesis of (+)-jasplakinolide

An enantioselective total synthesis of (+)-jasplakinolide is described. The synthesis of the polyketide template utilized a diastereoselective syn-aldol, ortho-ester Claisen rearrangement followed by efficient conversion to a cyanide. The β-amino acid uni

A synthesis of Jaspamide based on 1,2-metallate rearrangements of α-heteroalkenylmetal derivatives

Jaspamide (Jasplakinolide), a marine cyclodepsipeptide, was synthesised from tripeptide fragment 4 and (2S,4E,6R,8S)-8-benzoyloxy-2,4,6-trimethylnon-4-enoic acid (3). The tripeptide fragment was prepared from β-tyrosine derivative 6, Boc-2-bromoabrine (8)

Studies on the Novel Cyclodepsipeptides. A Total Synthesis of (+)-Jasplakinolide (Jaspamide)

Diastereocontrolled total synthesis of (+)-jasplakinolide (1) has been accomplished via coupling of the tetrapropionate-derived segment (9) with the tripeptide (10) followed by trichlorobenzoyl chloride-mediated macrolactonization.

Studies on cyclodepsipeptides - Part II : The total synthesis of jaspamide and geodiamolide-D

The total synthesis of cyclodepsipeptides jaspamide and geodiamolide D have been presented.