171626-76-9

Upstream product

• 67-56-1 methanol 
• 171626-75-8 1-[3-Chloro-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-4-(tetrahydro-pyran-2-yloxy)-butane-1,3-dione 
• 204187-89-3 4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-chloro-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-3,3-dimethoxy-butan-1-one 
• 204187-92-8 4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethoxy-butyryl chloride 
• 204187-86-0 4-[(tert-butyldimethylsilyl)oxy]-3,3-dimethoxybutanoic acid 
• 204187-88-2 2-bromo-3-chloro-1-(toluene-4-sulfonyl)-1H-pyrrole 
• 56164-42-2 3-chloro-1H-pyrrole-2-carbaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 171626-90-7 3-chloro-2-formyl-1-(p-toluenesulfonyl)pyrrole 
• 171626-91-8 2-acetyl-3-chloro-1-tosylpyrrole 
• 171626-92-9 1-[3-Chloro-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-ethanol 
• 171626-93-0 1-[3-Chloro-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-butan-1-one 

Downstream Products

• 171626-77-0 [5-(3-Chloro-1H-pyrrol-2-yl)-3-methoxy-furan-2-yl]-cyclohexyl-methanol 
• 188491-48-7 3-Chloro-2-(5-cyclohexylidenemethyl-4-methoxy-furan-2-yl)-pyrrole-1-carboxylic acid tert-butyl ester 
• 171626-78-1 3-Chloro-2-[5-(cyclohexyl-hydroxy-methyl)-4-methoxy-furan-2-yl]-pyrrole-1-carboxylic acid tert-butyl ester 
• 171626-79-2 2-(1-{5-[3-Chloro-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-3-methoxy-furan-2-yl}-vinyl)-pyrrole-1-carboxylic acid tert-butyl ester 
• 171626-83-8 7-{5-[3-Chloro-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-3-methoxy-furan-2-yl}-4,5-dihydro-indole-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Mild Friedel-Crafts Reactions Enable a Robust Synthesis of Roseophilin

An 11-step total synthesis of either enantiomer of roseophilin has been developed. The chemistry features effective production of a challenging carbocation on a macrocyclic segment 25 and a highly efficient intermolecular Friedel-Crafts alkylation reaction to integrate a complex furan-pyrrole unit 5 regioselectively with this carbocation under very mild reaction conditions.

Total synthesis of roseophilin

The first total synthesis of the antitumor agent roseophilin 1 is reported. Its intricate macrotricyclic core 2 is obtained by means of a new palladium-catalyzed manifold for the formation of ansa-bridged pyrroles which proceeds via vinyl oxirane 8 and allyl lactone 11 as key intermediates. After conversion of the latter into pyrrolophane 14, a base-induced elimination of the sulfone group followed by the Michael addition of a zincate onto the resulting enone 18 installs the isopropyl substituent in a stereoselective manner. The pyrrolylfuran side chain 3 of roseophilin is prepared from 4- methoxy-2(5H)-furanone (24) and methyl 4-chloropyrrole-2-carboxylate (26) as the starting materials. The appropriate building blocks 25a and 28 derived thereof are combined via a sequence comprising a directed metal-halogen exchange reaction, transmetalation of the resulting lithiopyrrole to the corresponding organozinc compound, a palladium-catalyzed cross coupling of the latter, and a subsequent acid-catalyzed closure of the resulting ketone 29 leading to the furan entity of the target. The triisopropylsilyl- protected side chain 3b is first deprotonated with n-BuLl and then transmetalated with CeCl3 to give a highly nucleophilic organocerium reagent, which readily attacks the sterically hindered 2- (trimethylsilyl)ethoxymethyl-protected keto pyrrole 2c. Deprotection and final dehydration of the tertiary alcohol derivative 30 thus obtained leads to the intact azafulvene chromophore of the natural product and completes our total synthesis of this alkaloid.

Synthesis of various model compounds for the conjugated heterocyclic ring system of antibiotic roseophilin

The title synthesis was accomplished starting with 3-chloro-2-formylpyrrole. The synthetic scheme featured one-pot preparation of the 4-methoxy-2-(pyrrol-2-yl)furan from the 2-acetoacetylpyrrole and coupling reactions of the C5-position of the