An efficient stereoselective synthesis of furanoverrillin (5), a highly functionalized core of verrillin (1), is reported. The synthetic strategy is based on constructing bicyclic lactone 17 prior to the 10-membered ring macrocyclization. The effect of the C4 methyl group on the furan reactivity is also discussed.

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 require h...

Synthesis of biaryl-containing macrocycles has been carried out through a four-step approach comprising two Ugi four component reactions and a Suzuki-Miyaura macrocyclization. This protocol allowed the synthesis of 12- and 14-membered macrocycles. Cytotoxic activity evaluation showed that some of the molecules were effective against leukemia, glioblastoma and lung cancer cell lines (IC50 = 4.0,...

SYNLETT 2005, No. 4, pp 0700–070204.03.2005 Advanced online publication: 22.02.2005 DOI: 10.1055/s-2005-863713; Art ID: Y04404ST © Georg Thieme Verlag Stuttgart · New York Abstract: The total synthesis of smenochromene D, an unusual ansa-terpenoid is described. The synthesis features an unprecedented macrocyclization proceeding through a biomimetic electrocyclization. The enantiomeric relations...

Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1-3 h). Moreover, when using Cys pseudoprolines as peptide macrocyclization-enhancing moieties a considerable reduction in reaction time was observed compared to a ...

The first asymmetric total synthesis and revision of the relative configuration of the 12-membered taumycin A macrocycle is described. Key to the success of this work was a novel α-keto ketene macrocyclization that provided an efficient means by which to access two diastereomers of the desired macrolide without the need to employ additional coupling agents or unnecessary oxidation state adjustm...

Nonribosomal peptide synthetases responsible for the production of macrocyclic compounds often use their C-terminal thioesterase (TE) domain for enzymatic cyclization of a linear precursor. The excised TE domain from the nonribosomal peptide synthetase responsible for the production of the cyclic decapeptide tyrocidine A, TycC TE, retains autonomous ability to catalyze head-to-tail macrocycliza...