ABSTRACT
A sequential CH functionalization strategy for the synthesis of the marine alkaloid dictyodendrinâ B is reported. Our synthesis begins from commercially available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural product.
Subject(s)
Carbazoles/chemistry , Carbazoles/chemical synthesis , Pyrroles/chemistry , Pyrroles/chemical synthesis , Chemistry Techniques, Synthetic , Hydrogen Bonding , Indoles/chemistry , Molecular StructureABSTRACT
Two palladium-catalysed amination protocols are deployed in the desymmetrisation of the complex dimeric alkaloid meso-chimonanthine. The power of these transformations is showcased in an efficient formal and total synthesis of the natural products hodgkinsine and hodgkinsine B, respectively.
Subject(s)
Chemistry Techniques, Synthetic/methods , Indoles/chemistry , Indoles/chemical synthesis , Pyrroles/chemistry , Amination , Catalysis , Molecular Structure , Palladium/chemistry , StereoisomerismSubject(s)
Indoles/chemical synthesis , Catalysis , Indoles/chemistry , Oxindoles , Palladium/chemistry , Pyrroles/chemistry , StereoisomerismABSTRACT
o-Halo benzoates can be combined with monoalkyl ureas in a tandem palladium-catalyzed arylation-ester amidation sequence to deliver quinazolinedione products. The reactions are regioselective for formation of the 3-N-alkyl isomers. Significant variation of both coupling partners is possible, allowing the synthesis of a diverse array of substituted quinazolinediones, exemplified by the preparation of a simple unsymmetric-dialkylated natural product. [reaction: see text]
