195873-89-3

Upstream product

• 195873-88-2 2-bromophenyl 2-diazo-2-phenylacetate 
• 95-56-7 2-hydroxybromobenzene 
• 611-71-2 MANDELIC ACID 
• 611-73-4 Benzoylformic acid 
• 195874-02-3 Oxo-phenyl-acetic acid 2-bromo-phenyl ester 

Downstream Products

• 195873-90-6 7-Bromo-2-oxo-3-phenyl-2,3-dihydro-benzofuran-3-carboxylic acid ethyl ester 
• 405519-72-4 7-bromo-3-hydroxymethyl-3-phenyl-3H-benzofuran-2-one 
• 405519-79-1 4-[3-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-2,3-dihydro-benzofuran-7-yl]-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-1-methoxymethyl-1H-indole 
• 405519-88-2 C₃₁H₂₁Cl₂N₃O₄ 
• 405519-84-8 C₃₁H₂₅N₃O₅ 
• 405519-83-7 C₃₁H₂₇N₃O₅ 
• 405519-86-0 C₃₀H₂₁N₃O₄ 
• 405519-85-9 C₃₁H₂₃N₃O₄ 
• 405519-80-4 {7-[3-(2-hydroxymethyl-oxazol-5-yl)-1-methoxymethyl-1H-indol-4-yl]-3-phenyl-2,3-dihydro-benzofuran-3-yl}-methanol 
• 405519-81-5 5-[4-(3-formyl-3-phenyl-2,3-dihydro-benzofuran-7-yl)-1-methoxymethyl-1H-indol-3-yl]-oxazole-2-carbaldehyde 
• 405519-76-8 3-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran 
• 405519-73-5 7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-3H-benzofuran-2-one 
• 405519-75-7 (7-bromo-3-phenyl-2,3-dihydro-benzofuran-3-ylmethoxy)-tert-butyl-dimethyl-silane 

Relevant academic research and scientific papers

Studies toward diazonamide A: Initial synthetic forays directed toward the originally proposed structure

A brief introduction into the chemistry of diazonamide A (1) is followed by first-generation sequences to access the originally proposed structure for this unusual marine natural product. These explorations identified a route capable of delivering a model compound possessing the complete heteroaromatic core of the natural product, highlighting in the process several unanticipated synthetic challenges which led both to new methodology as well as an improved synthetic plan that was successfully applied to fully functionalized intermediates.

SYNTHESIS OF DIAZONAMIDE "A" CORE

Using a novel samarium (II)-based macrocyclization cascade reaction, the entire highly strained ABCDEF aromatic core of diazonamide "A" and several novel analogies thereof are constructed.

Construction of the complete aromatic core of diazonamide A by a novel hetero pinacol macrocyclization cascade reaction

One of the most enticing natural products isolated in recent years and a serious challenge to synthetic chemists is represented by the potent anticancer agent diazonamide A (1). By utilizing a highly convergent approach, the ABCDEF macrocycle 2 was constr

Studies towards the synthesis of diazonamide A. Unexpected formation of a 3,4-bridged indole

Model studies towards the synthesis of the cytotoxic marine natural product diazonamide A are described. Three model 3-phenylbenzo[b]furan derivatives 5, 8 and 10 were prepared using rhodium(II) catalysed decomposition of the diazophenylacetate 3, Claisen rearrangement of the ether 7, and a classical intramolecular Friedel-Crafts reaction as key steps. Only the aromatic benzofuran system proved satisfactory in palladium coupling reactions; diazoacetyl(benzofuranyl)indole 18 was prepared by Suzuki coupling of (benzofuran-7-yl)boronic acid 11 with 4-bromoindole 14 to give 17, followed by diazo-transfer. Rhodium(II) catalysed decomposition of 18 in acetonitrile resulted in the formation of the 3,4-bridged indole 19 rather than the desired oxazole 20.