A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to t...

Nucleophilic ring-opening reactions of cyclic oxonium derivatives anionic boron hydrides are a convenient method their modification which opens practically unlimited prospects for incorporation into various macro- and biomolecules. This contribution provides an overview the synthesis reactivity nido-carborane as well half-sandwich complexes based on it.

A regioselective synthesis of oxepinones and azepinones in good to excellent yields from alkynylcyclopropanecarboxylic acid derivatives is described. This novel cycloisomerization cascade process consists of a nucleophilic addition followed by a cyclopropane ring-opening, where both donor and acceptor groups are required as substituents of the cyclopropane ring.

A novel doubly N-confused isophlorin (2) was prepared by the nucleophilic ring-opening reaction of N-confused, N-fused porphyrin (1) with benzenethiol. The structure, redox property and copper coordination ability of isophlorin 2 were investigated by various spectroscopic methods and theoretical calculations.

Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 --> 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols.

A new ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids was developed, which allows for one-pot synthesis of 1,4-benzothiazines in moderate to excellent yields. The cascade reaction was achieved through decarboxylative coupling, nucleophilic ring-opening reaction and intramolecular hydroamination process.

Stable, water-soluble aminosugar staurosporine, K-252a and rebeccamycin analogs have been prepared by nucleophilic opening of C(2)-symmetric N-activated bis-aziridines by bis-indolylmaleimides. This divergent strategy allows the synthesis of unsymmetrical substituted derivatives and provides an easy access to the piperidine and pyrrolidine analogs.

α,β-Unsaturated oximes underwent electrophilic epoxidation with in-situ-generated dimethyldioxirane to give the corresponding epoxides in good yields. This reaction is an example of “carbonyl umpolung” by transformation α,β-unsaturated ketones their oximes. Nucleophilic ring-opening reactions afforded α-substituted products. Shi asymmetric proceeded moderate enantioselectivity.

We report here a new voltammetric method for the sensitive and selective determination of Hg(2+) based on rational covalent functionalization of graphene oxide with cysteamine to form cysteamine-functionalized graphene through nucleophilic ring-opening reaction between the epoxy of graphene oxide and the amino group of cysteamine in KOH solution.