58045-93-5

Upstream product

• 6379-72-2 1,2-dimethoxy-4-(E)-propenylbenzene 
• 186581-53-3 diazomethane 
• 1140478-56-3 endiandrin B 

Downstream Products

• 6379-72-2 1,2-dimethoxy-4-(E)-propenylbenzene 
• 62211-17-0 1α-(3,4-Dimethoxyphenyl)-2β-methyl-3β-ethyl-5,6-dimethoxyindan 
• 118353-36-9 1α,5β-Di-(3,4-dimethoxyphenyl)-2β,3α,4α-trimethyl-7,8-dimethoxy-1,2,2a(Hα),3,4,5-hexahydroacenaphthylene 
• 118353-37-0 1β,5β-Di-(3,4-dimethoxyphenyl)-2α,3α,4α-trimethyl-7,8-dimethoxy-1,2,2a(Hα),3,4,5-hexahydroacenaphthylene 
• 118353-38-1 1β,5β-Di-(3,4-dimethoxyphenyl)-2α,3α,4α-trimethyl-7,8-dimethoxy-1,2,2a(Hβ),3,4,5-hexahydroacenaphthylene 
• 118298-00-3 2-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-1,3-dimethylnaphthalene 
• 118298-01-4 1α,5α-Di-(3,4-dimethoxyphenyl)-2β,3α,4β-trimethyl-7,8-dimethoxy-1,2,2a(Hα),3,4,5-hexahydroacenaphthylene 
• 118298-02-5 1α,4β-Di-(3,4-dimethoxyphenyl)-2β,3α,5α-trimethyl-7,8-dimethoxy-1,2,2a(Hα),3,4,5-hexahydroacenaphthylene 
• 118353-39-2 1β,4β-Di-(3,4-dimethoxyphenyl)-2α,3α,5α-trimethyl-7,8-dimethoxy-1,2,2a(Hα),3,4,5-hexahydroacenaphthylene 

Relevant academic research and scientific papers

Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum

Chemical investigations of the DCM extract from the roots of Endiandra anthropophagorum resulted in the isolation of a new cyclobutane lignan endiandrin B (1), together with the known natural products, endiandrin A (2), and (-)-dihydroguaiaretic acid (3).

Radical-Cation-Initiated Diels-Alder Di- and Trimerization of 3,4-Dimethoxypropenylbenzene: Stereochemical Correlation with the Lignans Galbulin and Isogalbulin

Diels-Alder reactions of methylisoeugenol (3,4-dimethoxypropenylbenzene, 1) initiated by the radical cation tris(p-bromophenyl)aminium hexachloroantimonate (BAHA) lead to the naphthalene regioisomers 7 and 8 as well as the trimers 9-15.The radical-cation origins of these products have been established through detailed regio- and stereochemical studies which indicate that the initial Diels-Alder step proceeds with (1) a lack of regiospecificity and (2) a preference for the endo rather than the exo reaction configuration.The number of regio- and stereoisomers is substantially reduced in the BAHA-initiated rearrangement of the cyclobutane 16, which affords only the naphthalene 7 and the trimers 11-13.While the initial Diels-Alder step provides the same stereochemistry that is found in the lignans galbulin (3) and isogalbulin (5), the formation of the regioproducts (8, 14, and 15) and the involvement of a third unit of 1 to form the trimers (9-15) preclude any straightforward correlation of radical-cation Diels-Alder reactions with the biosynthesis of the aryltetralin lignans.