ABSTRACT
A general synthesis of dibenzoxepine lactams has been developed using a one-pot Cu-catalyzed etherification/aldol condensation cascade reaction. The reaction of 4-hydroxyisoindolin-1-one with a wide range of 2-bromobenzaldehydes in the presence of a copper catalyst provided various aristoyagonine derivatives in good yields.
Subject(s)
Benzoxepins/chemical synthesis , Copper/chemistry , Isoquinolines/chemical synthesis , Lactams/chemical synthesis , Aldehydes/chemistry , Benzaldehydes/chemistry , Benzoxepins/chemistry , Catalysis , Isoquinolines/chemistry , Lactams/chemistry , Molecular Structure , StereoisomerismABSTRACT
The first complete synthesis of laetevirenol A was performed in nine steps via intramolecular Friedel-Crafts alkylation in a trans-selective manner. The key phenanthrene intermediate was synthesized by a one-pot Suzuki-Miyaura coupling and an aldol condensation cascade reaction.
Subject(s)
Phenanthrenes/chemistry , Phenanthrenes/chemical synthesis , Alkylation , Catalysis , Molecular Structure , StereoisomerismABSTRACT
A one-pot transition-metal-free, base-mediated synthesis of dibenzo[b,f]oxepins was developed. The reaction of 2-halobenzaldehydes with (2-hydroxyphenyl)acetonitriles proceeds via a sequential aldol condensation and intramolecular ether formation reaction in the presence of Cs(2)CO(3) and molecular sieves in toluene.
Subject(s)
Benzaldehydes/chemistry , Benzene/chemistry , Oxepins/chemical synthesis , Isomerism , Models, Molecular , Molecular StructureABSTRACT
Highly stereoselective, palladium-catalyzed α-arylation reactions of 3-aryl-1-indanones with aryl bromides are described. The use of sodium tert-butoxide as a base in this process is required to elevate the efficiencies and stereoselectivities of these reactions. The new methodology was successfully applied to a highly efficient route for the asymmetric synthesis of (+)-pauciflorol F.
Subject(s)
Hydrocarbons, Brominated/chemistry , Indans/chemistry , Palladium/chemistry , Stilbenes/chemical synthesis , Catalysis , Molecular Structure , Stereoisomerism , Stilbenes/chemistryABSTRACT
A series of natural aristolactams and their analogues have been prepared and evaluated for antitumor activity against human cancer cells, including multi-drug resistant cell lines. Naturally occurring aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and sauristolactam showed moderate antitumor activities in selected cell lines. However, several synthetic aristolactam derivatives exhibited potent antitumor activities against a broad array of cancer cell lines with GI(50) values in the submicromolar range.
Subject(s)
Antineoplastic Agents/chemical synthesis , Heterocyclic Compounds, 4 or More Rings/chemical synthesis , Lactams/chemical synthesis , Antineoplastic Agents/chemistry , Antineoplastic Agents/toxicity , Aporphines/chemical synthesis , Aporphines/chemistry , Aporphines/toxicity , Cell Line, Tumor , Drug Screening Assays, Antitumor , Heterocyclic Compounds, 4 or More Rings/chemistry , Heterocyclic Compounds, 4 or More Rings/toxicity , Humans , Lactams/chemistry , Lactams/toxicityABSTRACT
A common strategy for the synthesis of a 7-membered-ring system with a Suzuki-Miyaura coupling followed by an acid/base-promoted intramolecular aldol condensation reaction has been developed. The reaction of 2'-bromoacetophenones with 2-formylphenylboronic acids in the presence of Pd(OAc)(2) and CataCXium PIntB L8 efficiently provided biaryl compounds, which were transformed to a wide array of dibenzo[a,c]cyclohepten-5-ones in excellent yields by a sequential treatment with p-TsOH, followed by 10% aq NaOH.
