3889-89-2

Upstream product

• 23523-94-6 1-methoxy-3-methoxycarbonyl-9H-carbazole 
• 182261-83-2 methyl 1-hydroxy-9H-carbazole-3-carboxylate 
• 41608-64-4 methyl 3-methoxy-4-aminobenzoate 
• 175153-75-0 3-methoxy-4-trifluoromethane-sulfonyloxy-benzoic acid methyl ester 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 140472-69-1 3-bromo-5-hydroxy-benzoic acid 
• 56709-70-7 3-bromo-5-methoxy-benzoic acid methyl ester 
• 889654-06-2 3-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester 

Relevant academic research and scientific papers

Total synthesis of carbazole alkaloids

A Suzuki-Miyaura cross coupling, followed by triphenylphosphine mediated Cadogan reductive cyclization sequence provided efficient access to a series of carbazole alkaloids. In the present work, this approach was applied to the total synthesis of mukonine, clauszoline K, koenoline, murrayanine, murrayafoline A, mukoeic acid, glycoborine, glycozolicine, mukolidine, mukoline, glycozoline, 3-methoxy-9H-carbazole-1-carboxylic acid methyl ester, (3-methoxy-9H-carbazol-1-yl)-methanol, 3-methoxy-9H-carbazole-1-carbaldehyde, 3-methoxy-9H-carbazole-1-carboxylic acid, 2-methyl-9H-carbazole and nonsteroidal anti-inflammatory drug (NSAID) carprofen and its derivatives.

Palladium-Catalyzed Formal [4+2] Cycloaddition of Benzoic and Acrylic Acids with 1,3-Dienes via C—H Bond Activation: Efficient Access to 3,4-Dihydroisocoumarin and 5,6-Dihydrocoumalins

We report a palladium-catalyzed formal intermolecular [4+2] cycloaddition of benzoic and acrylic acids with 1,3-dienes including the stock chemicals 1,3-butadiene and isoprene leading to synthetically useful 3,4-dihydroisocoumarins and 5,6-dihydrocoumalins. Stepwise C—H bond cleavage and annulation are likely involved in the reaction pathway. The synthetic potential of the methodology was demonstrated by two short derivatizations and total synthesis of natural product Clausamine B.

Total synthesis of diverse oxygenated carbazoles by modified aromatization using molecular iodine

A convenient route has been developed for mono and dioxygenated carbazole alkaloids from 1-oxotetrahydrocarbazoles. The key step of the synthetic route is the aromatic process of 1-oxotetrahydrocarbazoles using molecular iodine. To our knowledge, this is

A new two step route to 1-hydroxy-9H-3-carbazolecarboxylic acid derivatives from 3-formylindole. Application to the synthesis of mukonine

Carbazole alkaloid mukonine 6b was prepared from 3-formylindole in three steps (32% overall yield). The key step was the base-promoted cyclization of a mixed anhydride of mono ester mono acid 5.

Transition metal-diene complexes in organic synthesis - 16.1 Iron-mediated total synthesis of 1-oxygenated carbazole alkaloids

Using a methodology of consecutive iron-induced C - C and C - N bond formation we describe the total synthesis of murrayafoline A, murrayaquinone A, koenoline, murrayanine, mukoeic acid, and mukonine.