[reaction: see text]. The copper acetate mediated intramolecular O-arylation of phenols with phenylboronic acid pseudopeptides is the key step in the preparation of macrocyclic biphenyl ether hydroxamic acid inhibitors of collagenase 1 and gelatinases A and B. The intramolecular macrocyclization was found to be mild and tolerant of common chemical functionality. This methodology should provide ...

Nannocystin A is a 21-membered cyclodepsipeptide showing remarkable anticancer properties. Described is the total synthesis of nannocystin A, which features an asymmetric vinylogous Mukaiyama aldol reaction for efficient assembly of the penultimate open-chain precursor and a pivotal intramolecular Heck cross-coupling for the final macrocyclization.

The Richman-Atkins cyclization remains one of the most widely used methods for the preparation of macrocyclic polyamines. The use of beta-trimethylsilylethanesulfonamides (SES-sulfonamides) for the preparation of polyazamacrocyclic compounds is described. This expands existing Richman-Atkins sulfonamide macrocyclization methodology, and it successfully enables preparation of labile polyaza[n](1...

Some new macrocyclic dibenzotetraoxadiamides, tribenzotetraoxadimides, tribenzopentaoxadiamide, tribenzohexaoxadiamide, and tetrabenzoheptaoxadiamide 15-22 have been prepared. These compounds were obtained in the macrocyclization step by reacting the diamines 6 and 7 with appropriate dicarboxylic acid dichlorides 8-14. The cyclization does not require high dilution techniques or template ef...

This review is dedicated to the different varieties of macrocycles synthesis bearing indole units in their architecture by metal-catalyzed strategies. The progress new macrocyclization approaches persisted be a keen area research. Macrocycles contain wide variety molecules, and among those, heteroaryl motifs are valuable constituents that provide an attractive feature macrocyclic systems. Indol...

Some new macrocyclic dibenzotrioxadiamides, dibenzotetraoxadiamide, dibenzopentaoxadiamide, dibenzothiatrioxadiamide, tribenzotrioxadiamides and tetrabenzohexaoxadiamide (14-21), (26) and (27) have been prepared. These compounds were obtained in the macrocyclization step by reacting the diamine (4) with appropriak dicaxboxylic acid dichlorides (5-13) and (24). The cyclization does not requ...

Macrocycles constitute an attractive structural class of molecules for targeting biomolecular interfaces with high affinity and specificity. Here, we report systematic studies aimed at exploring the scope and mechanism of a novel chemo-biosynthetic strategy for generating macrocyclic organo-peptide hybrids (MOrPHs) through a dual oxime-/intein-mediated ligation reaction between a recombinant pr...

A glutathione S-transferase (GST) catalyzed macrocyclization reaction for peptides up to 40 amino acids in length is reported. GST catalyzes the selective S(N)Ar reaction between an N-terminal glutathione (GSH, γ-Glu-Cys-Gly) tag and a C-terminal perfluoroaryl-modified cysteine on the same polypeptide chain. Cyclic peptides ranging from 9 to 24 residues were quantitatively produced within 2 h i...

The enantioselective total synthesis of rumphellaone A has been accomplished in 12 steps via a diastereoselective gold(I)-catalyzed [2 + 2] macrocyclization of a 1,10-enyne as the key step to build the cyclobutene moiety. This concise approach has also led to the total synthesis of husinone.