441287-32-7

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 62674-12-8 3,4-dichloro-5H-furan-2-one 
• 70744-47-7 (p-methoxyphenyl)tri-n-butylstannane 
• 1245731-24-1 C₅H₂ClF₃O₅S 
• 1245731-25-2 C₁₁H₉ClO₅S 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 

Downstream Products

• 441287-27-0 (Z)-5-[1-(3-bromo-4-methoxyphenyl)methylidene]-3-chloro-4-(4-methoxyphenyl)-2(5H)-furanone 
• 446044-05-9 3-(3,4,5-trimethoxyphenyl)-4-(4-methoxyphenyl) furan-2(5H)-one 
• 136781-95-8 rubrolide B 
• 3516-65-2 4-(4-methoxyphenyl)furan-2(5H)-one 
• 7706-90-3 4-(4-hydroxyphenyl)furan-2(5H)-one 
• 136762-98-6 (Z)-4-(4-hydroxyphenyl)-5-(4-methoxybenzylidene)furan-2(5H)-one 
• 136762-97-5 4-(4-hydroxyphenyl)-5-[(Z)-(4-hydroxyphenyl)methylidene]furan-2-one 

Relevant academic research and scientific papers

Palladium-catalyzed hydrodehalogenation of butenolides: An efficient and sustainable access to β-arylbutenolides

Several α-unsubstituted β-arylbutenolides have been prepared in 69–92% yield by reductive dehalogenation of α-halo-β-arylbutenolides. The latter were assembled in a single-step from α,β-dihalobutenolides, which are accessible on a large-scale from biomass-derived furfural. Our dehalogenation protocol is illustrated by a new synthesis of the marine antibiotics rubrolide E and F, and 3″-bromorubrolide F.

Late-Stage Bromination Enables the Synthesis of Rubrolides B, I, K, and O

A concise and efficient synthesis of the marine natural products rubrolides B, I, K, and O was accomplished in 3–4 steps from commercially available 3,4-dichloro-2(5H)-furanone. Key steps include: (i) a site-selective Suzuki cross-coupling, (ii) a vinylogous aldol condensation, and (iii) a late-stage bromination. The latter reaction allowed functionalization of the aromatic rings in a highly regioselective fashion, enabling rapid access to the target rubrolides from common precursors.

Synthesis of α-halobutenolides using the nucleophilicity of magnesium alkylidene carbenoids

α-Halobutenolides were synthesized from halomethyl p-tolyl sulfoxides, α-bromoketones, and phenyl chloroformate in three steps using the nucleophilicity of magnesium alkylidene carbenoids. The reaction of ?-bromoketones with [halo(p-tolylsulfinyl)methyl]lithiums and the subsequent basification of the reaction mixture using an aqueous NaOH solution afforded 1-chloro-3-hydroxyprop-1-enyl p-tolyl sulfoxides in 83-99% yield. A phenoxycarbonyl group was then introduced to the hydroxyl group of the sulfoxides by reacting with phenyl chloroformate in the presence of pyridine. The sulfoxide/magnesium exchange reaction of the cyclization precursors with i-PrMgCl·LiCl led to the formation of α-halobutenolides in moderate to good yields.

Synthesis of the human aldose reductase inhibitor rubrolide L

The first synthesis of rubrolide L, a marine ascidian butenolide and a potent inhibitor of human aldose reductase, has been achieved by two tactically distinct pathways in 4-5 steps and 37-42% overall yield from commercially available 3-chlorotetronic acid.

Mucochloric acid: A useful synthon for the selective synthesis of 4-aryl-3-chloro-2(5H)-furanones, (Z)-4-aryl-5-[1-(aryl)methylidenel-3-chloro-2(5H)-furanones and 3,4-diaryl-2(5H)-furanones

3,4-Dichloro-2(5H)-furanone, which has been prepared efficiently from mucochloric acid, has been transformed selectively into 4-aryl-3-chloro-2(5H)-furanones either by Suzukior Stille-type reactions. These monochloro derivatives have been used as precursors either to (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones, including naturally occurring rubrolide M, or to unsymmetrical 3,4-diaryl-2(5H)-furanones. Some 2(5H)-furanone derivatives so prepared have been found to exhibit significant cytotoxic activity in vitro against the NCI three-cell-line panel, but limited cytotoxicity against the NCI human tumor 60 cell-line panel. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Total synthesis of rubrolide M and some of its unnatural congeners

Two protocols have been developed for the Pd-catalyzed regioselective synthesis of 4-aryl-3-chloro-2(5H)-furanones starting from 3,4-dichloro-2(5H)-furanone. These monochloro derivatives have then been used as precursors to (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones including naturally-occurring rubrolide M.