Asymmetric total synthesis of (+)-jasplakinolide

Chu, Kent S.; Negrete, George R.; Konopelski, Joseph P.

doi:10.1021/jo00017a037

Cited by 91 publications

(30 citation statements)

References 5 publications

(15 reference statements)

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“…However, macrolactamization does not have a monopoly, as a few notable examples of macrolactonization have been reported. Thus jasplakinolide (22) was cyclized at point (a) using DCC/DMAP.TFA (79% yield) [159] and using DCC only [160] in 36% yield. It is implied that DMAP.TFA in the former example raises the effective concentration of protons thus catalysing macrolactonization.…”

Section: Cyclodepsipeptidesmentioning

confidence: 99%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

409

241

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Constricting the peptide backbone into a more defined conformational form through cyclization is an activity evolved in nature and in synthetic work, the latter straddling only the most recent decades. The resulting conformational constraints increase the probability of an optimum response with bio-receptors. The purpose of this review is to highlight developments that have proved to be reasonably efficient in the macrocyclization of linear precursors into cyclic peptides and depsipeptides.

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Section: Cyclodepsipeptidesmentioning

confidence: 99%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

409

241

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“…Some of these compounds show high biological activity as antibiotics (e.g. monamycins, [44] echinomycin [45] ), insecticides, [46] antitumor agents (e.g. bouvardin [47] ) and antiinflammatory peptides (e.g.…”

Section: N-alkylated Peptidesmentioning

confidence: 99%

Peptidomimetics – A Versatile Route to Biologically Active Compounds

2009

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Proteins are vital for basically every known organism. Therefore the investigation of their structure, the development of a deeper understanding of protein-protein interactions and the design of novel peptides, which selectively interact with proteins are fields of active research. Small peptides consisting of the 20 natural amino acids typically show high conformational flexibility and a low in-vivo stability which hampers their application as tools in medicinal diagnostics or molecular biology. One very versatile strategy to overcome such drawbacks is the use of peptidomimetics. These are small

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“…The method allows for mono-N-methylation without the problems associated with dimethylation and no methylation of imines. Chu et al [69] exploited this strategy by reducing N-formyl-D-tryptophan methyl ester with BH 3 ÁSMe 2 . The reduction gave, after work-up, N-methyl-D-tryptophan methyl ester in 56% yield.…”

Section: Borane Reduction Of Amidesmentioning

confidence: 99%