An efficient acid-promoted domino Friedel-Crafts (FC) acylation/alkylation reaction has been developed for the construction of the core 6,5,6-ABC tricyclic skeleton of taiwaniaquinoids. The formal total syntheses of diterpenoids (+/-)-taiwaniaquinol B and (+/-)-dichroanone based on this strategy have been achieved.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol800513vDOI Listing

Publication Analysis

Top Keywords

domino friedel-crafts
8
friedel-crafts acylation/alkylation
8
acylation/alkylation reaction
8
+/--taiwaniaquinol +/--dichroanone
8
application domino
4
reaction formal
4
formal syntheses
4
syntheses +/--taiwaniaquinol
4
+/--dichroanone efficient
4
efficient acid-promoted
4

Similar Publications

A transition metal-free, atom-economical, and highly stereospecific synthetic approach to Friedel-Crafts-type alkylation of arenes/heteroarenes has been developed. The protocol involves the catalytic aminium radical-cation salt (Magic Blue)-initiated S2-type nucleophilic ring opening of activated aziridines with arenes/heteroarenes to give the corresponding 2,2-diarylethylamines up to 99% yield and 85% ee (for nonracemic aziridines) in a very short reaction time. Moreover, on reaction with 1,3-dimethylindole and benzofuran, aziridines undergo domino-ring-opening cyclization (DROC) to give the various biologically significant heterocyclic scaffolds in moderate to good yields.

View Article and Find Full Text PDF

An asymmetric Michael/Friedel-Crafts cascade reaction with Morita-Baylis-Hillman (MBH) nitroallylic esters and 3-pyrrolyloxindoles has been developed for the stereoselective construction of spirooxindole-containing tetrahydroindolizines. A range of tetracyclic scaffolds possessing three consecutive chiral centers, including an all-carbon quaternary stereocenter, were generated in 53-85% isolated yields with high diastereoselectivities and enantiopurities (≥3:1 dr, 50-98% ee). A newly synthesized bifunctional secondary amine/squaramide organocatalyst was demonstrated to exhibit better stereochemical control than their tertiary analogues.

View Article and Find Full Text PDF

This article demonstrates recent innovative cascade annulation methods for preparing functionalized carbazoles and their related polyaromatic heterocyclic compounds enabled by Lewis acid catalysts. Highly substituted carbazole scaffolds were synthesized Lewis acid mediated Friedel-Crafts arylation, electrocyclization, intramolecular cyclization, cycloaddition, C-N bond-formations, aromatization and cascade domino reactions, metal-catalyzed, iodine catalyzed reactions and multi-component reactions. This review article mainly focuses on Lewis acid-mediated recent synthetic methods to access a variety of electron-rich and electron-poor functional groups substituted carbazole frameworks in one-pot reactions.

View Article and Find Full Text PDF

The reaction of -phenyl iminoborane with benzaldehyde yielding a fused aromatic compound, recently reported by Liu et al., has been studied within the Molecular Electron Density Theory (MEDT). Formation of the fused aromatic compound is a domino process that comprises three consecutive reactions: (i) formation of a weak molecular complex between the reagents; (ii) an intramolecular electrophilic attack of the activated carbonyl carbon of benzaldehyde on the position of the -phenyl substituent of iminoborane; and (iii) a formal 1,3-hydrogen shift yielding the final fused aromatic compound.

View Article and Find Full Text PDF

The synthesis of substituted aza- and oxaazaisowurtzitanes via direct condensation is challenging. The selection of starting ammonia derivatives is very limited. The important step in developing alternative synthetic routes to these compounds is a detailed study on their formation process.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!