445218-28-0

Downstream Products

• 19438-10-9 methyl 3-hydroxybenzoate 
• 1359715-00-6 2-(2,3,4-tribromo-5-methoxyphenyl)ethanamine hydrochloride 
• 1359715-02-8 C₁₄H₁₈Br₃NO₃ 
• 1359715-04-0 C₁₅H₁₉Br₃N₂O₂ 
• 1359741-01-7 C₂HF₃O₂*C₉H₁₀Br₃NO 
• 1359715-20-0 C₈H₇Br₃O₂ 
• 1359714-96-7 2,3,4-tribromo-5-methoxybenzaldehyde 
• 1359714-98-9 (E)-2,3,4-tribromo-1-methoxy-5-(2-nitrovinyl)benzene 
• 1359741-00-6 C₉H₁₀Br₃NO 
• 920752-13-2 methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate 
• 920752-12-1 5-allyloxy-2,3,4-tribromo-benzoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of reported and revised structures of amathamide D and synthesis of convolutamine F, H and lutamide A, C

Total synthesis of the published structure of amathamide D is described. Methyl 2,3,4-tribromo-5-hydroxybenzoate was selected as starting compound because it is readily accessible via acid-mediated Grob fragmentation- aromatization reaction of 1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5- en-2-one. The aforementioned ester was transformed into the reported structure of amathamide D through methylation of a hydroxyl group and conversion of the ester moiety to a β-aminoethyl side chain. The NMR data of the synthetic compound did not conform to the reported natural product structure possessing contiguously positioned β-aminoethyl side chain, a set of three adjacent bromines, and a methyl ether linkage on the phenyl ring. This prompted us to redefine the natural product structure by synthesizing a product whose spectral data exactly matched with the reported data of amathamide D. The convolutamine H, with completely substituted phenyl ring adorned with an extra methyl ether functional group, has also been synthesized by application of Grob fragmentation-aromatization strategy to 3-(benzyloxy)-1,4,5,6-tetrabromo-7,7- dimethoxybicyclo[2.2.1]hept-5-en-2-one. This approach furnished directly methyl 2,3,4-tribromo-5,6-dimethoxybenzoate, which was converted straightforwardly into convolutamine H. Further, synthesis of convolutamine F and lutamide A and C is also described.

Rearrangement of 1,4,5,6-tetrahalo-7,7-dimethoxybicyclo[2.2.1]-hept-5-en-2-ones to phenolic derivatives

A simple Diels-Alder route leading to methyl 2,3,4-trihalo-5-hydroxybenzoates via thermal Grob-type rearrangement of easily accessible 1,4,5,6-tetrahalo-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-one with concomitant methyl halide elimination is described.