An expeditious assembling of fused poly-heterocyclic structures having a N(Acyl), N(aryl)-Acetal core has been accomplished by cascade reaction ortho-functionalized anilines with 2-formylbenzonitrile and subsequent intramolecular N-amidic cyclization on different electrophilic carbons. The syntheses have finalized using both cathodically-initiated conventional base-catalyzed methods comparing t...

The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF 3 ·Et 2 O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety electron-rich aromatics via Friedel–Crafts alkylation. This cascade Prins/Friedel–Crafts cyclization protocol paves expedient path to medicinally useful 4-aryltetralin-2-ol an...

reactions of n-isocyaniminotriphenylphosphorane with cyclopentanone have been studied in the presence of aromatic carboxylic acids and primary amines, proceeds smoothly at room temperature under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives by an intramolecular aza-wittig cyclization in ch2cl2 in excellent yields. the structures of the products were deduced from...

The excised C-terminal thioesterase (TE) domain from the multidomain tyrocidine nonribosomal peptide synthetase (NRPS) was recently shown to catalyze head-to-tail cyclization of a decapeptide thioester to form the cyclic decapeptide antibiotic tyrocidine A [Trauger, J. W., Kohli, R. M., Mootz, H. D., Marahiel, M. A., and Walsh, C. T. (2000) Nature 407, 215-218]. The peptide thioester substrate ...

The synthesis of 6H-benzo[c]chromenes from unactivated 2-bromo aryl benzyl ethers was studied through two approaches: (i) the transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution; and (ii) the intramolecular cyclization via direct C–H arylation catalysed by PdCl2(MeCN)2. Having developed the most efficient method, a 17-membered chromene ...

The seed oil of Euphorbia lathyris L. contains a series of macrocyclic diterpenoids known as Euphorbia factors. They are the current industrial source of ingenol mebutate, which is approved for the treatment of actinic keratosis, a precancerous skin condition. Here, we report an alcohol dehydrogenase-mediated cyclization step in the biosynthetic pathway of Euphorbia factors, illustrating the or...

The synthesis of non-racemic 5-membered cyclic carbonates from abundant alcohols is reported. Conversion the alcohol into an azanyl carbonate followed by a chiral-at-ruthenium catalyzed cyclization to provide chiral in yields up 95% and with 99% ee. This new synthetic method proposed proceed through nitrene-mediated intramolecular C(sp 3 )−H oxygenation which includes very unusual 1,7-hydrogen ...