117828-32-7

Upstream product

• 58327-37-0 α-Chloro-α-(4-methoxyphenyl)acetonitrile 
• 108-73-6 3,5-dihydroxyphenol 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 15485-66-2 2,4,6-trihydroxy-4'-methoxydeoxybenzoin 
• 136850-29-8 3-<4,6-dimethoxy-2-(4-methoxyphenyl)-3-oxo-2,3-dihydrobenzofuran-2-yl>-3-phenylpropanal 
• 117828-34-9 4,6-dimethoxy-2-(4-methoxyphenyl)-2-(2-cyanoethyl)-3-benzofuranone 
• 117828-35-0 (±)-(3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one 
• 117828-37-2 3-[3-Hydroxy-4,6-dimethoxy-2-(4-methoxy-phenyl)-2,3-dihydro-benzofuran-2-yl]-propionitrile 
• 117828-43-0 3-[4,6-Dimethoxy-2-(4-methoxy-phenyl)-3-oxo-2,3-dihydro-benzofuran-2-yl]-3-phenyl-propionitrile 
• 117828-36-1 (3aS,8bS)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-trimethylsilanyloxy-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one 
• 117828-45-2 (3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one 
• 117828-46-3 (3aS,8bS)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-8b-trimethylsilanyloxy-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one 
• 1160457-34-0 methyl 3-(4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran-3-yl)-3-oxopropanoate 
• 1160457-03-3 methyl 2-(4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran-3-carbonyl)-3-phenylacrylate 
• 1357016-39-7 C₂₀H₂₀O₆ 
• 1357016-41-1 6,8-dimethoxy-1-((4-methoxybenzyl)oxy)-3a-(4-methoxyphenyl)-3,3a-dihydro-2H-cyclopenta[b]benzofuran-2-one 
• 1357016-42-2 C₂₈H₂₆O₆ 

Relevant academic research and scientific papers

Synthesis and antitumor activity of sacroflavonoside

Sacroflavonoside, a new derivative of diphenylethene, was isolated from Artemisia sacrorum, which have been found to possess the inhibitory effect on the proliferation of gastric carcinoma cells (MKN-45) in vitro in our previous studies. With anisaldehyde (SM-A) as starting material, the sacroflavonoside was synthesized by nucleophilic addition, electrophilic substitution and dehydration cyclization. The structure of sacroflavonoside was established by 1 D (1H NMR and 13C NMR) and 2 D-NMR (HSQC and HMBC) spectral analysis. The antitumor activity and potential mechanism against MKN-45 cells of sacroflavonoside were evaluated in vitro. The results showed that sacroflavonoside could significantly induce MKN-45 cells apoptosis and autophagy by increasing the expression of Bax, Caspase-3, Beclin1 and LC3-II proteins and decreasing the expression of Bcl-2 protein at low micromole level. This investigation provided a valuable lead structure for the development of antitumor drugs.

Total synthesis of (±)-rocaglamide via oxidation-initiated nazarov cyclization

This article describes the evolution of a Nazarov cyclization-based synthetic strategy targeting the anticancer, antiinflammatory, and insecticidal natural product (±)-rocaglamide. Initial pursuit of a polarized heteroaromatic Nazarov cyclization to construct the congested cyclopentane core revealed an unanticipated electronic bias in the pentadienyl cation. This reactivity was harnessed in a successful second-generation approach using an oxidation-initiated Nazarov cyclization of a heteroaryl alkoxyallene. Full details of these two approaches are given, as well as the characterization of undesired reaction pathways available to the Nazarov cyclization product. A sequence of experiments that led to an understanding of the unexpected reactivity of this key intermediate is described, which culminated in the successful total synthesis of (+)-rocaglamide.

Synthesis of the Novel Anti-leukaemic Tetrahydrocyclopentabenzofuran, Rocaglamide and Related Synthetic Studies

Two approaches to the rocaglamide tricyclic skeleton are described.The first, which employs an unusual dithianyl anion to carbonyl addition reaction, provides access to α-phenyl rocaglamide analogues.The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both α- and β-phenyl substituents.A total synthesis of rocaglamide, in racemic form, is described using this second approach.The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield > 6percent.The synthesis of 1-epi-rocaglamide 29b is also described.