487027-13-4

Upstream product

• 75-52-5 nitromethane 
• 133871-69-9 2,4,6-tribromo-5-methoxybenzaldehyde 
• 1359715-22-2 C₉H₈Br₃NO₄ 
• 100-83-4 meta-hydroxybenzaldehyde 
• 2737-22-6 2,4,6-tribromo-3-hydroxybenzaldehyde 

Downstream Products

• 487027-14-5 2-(2,4,6-tribromo-3-methoxyphenyl)-2-(thiophenyl)-1-nitroethane 
• 1359715-06-2 2-(2,4,6-tribromo-3-methoxyphenyl)ethanamine 
• 112515-27-2 C₁₅H₁₉Br₃N₂O₂ 
• 294210-56-3 lutamide A 
• 487027-16-7 (2S)-N-[2-(2,4,6-tribromo-3-methoxyphenyl)-2-(thiophenyl)ethyl]-1-methyl-2-pyrrolidinecarboxamide 
• 487027-15-6 2-(2,4,6-dibromo-3-methoxyphenyl)-2-(thiophenyl)-1-aminoethane 

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.

Asymmetric synthesis of amathamides A and B: Novel alkaloids isolated from Amathia wilsoni

Syntheses of the amathamides A and B ((2S)-N-[(E and Z)-2(2,4-dibromo-5-methoxyphenylethenyl]-1-methyl-2-pyrrolinecarboxamides), new alkaloids isolated from the Tasmanian marine bryozoan Amathia wilsoni, were accomplished by a sequence of reactions starting from 3-hydroxybenzaldehyde.