79606-73-8

Upstream product

• 63320-66-1 phyltetralin 
• 10351-88-9 (+)-phyllanthin 
• 138737-28-7 bromophyllanthin 
• 252750-96-2 C₂₅H₃₆O₇ 
• 252750-94-0 (2S,3S)-1,4-Bis-(3,4-dimethoxy-phenyl)-2,3-bis-methoxymethyl-butan-2-ol 
• 10351-88-9 phyllanthin 

Downstream Products

• 5811-91-6 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene 
• 741292-74-0 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carboxylic acid 
• 741292-79-5 8-bromo-3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde 
• 741292-76-2 5-(3,4-dihydroxy-phenyl)-6,7-dimethyl-naphthalene-2,3-diol 
• 741292-75-1 4,5,3',4'-tetrahydroxy-2,7'-cycloligna-7,7'-diene-9,9'-lactone 
• 6258-38-4 dehydrodimethylconidendrin 

Relevant academic research and scientific papers

Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans

Ten lignans (2-11) and a series of azalignans including 1-aryl-pyrronaphthalenes 20-24 and 3-N-alkylaminomethyl-1-arylnaphthalenes 25-28, structurally related to two HIV reverse transcriptase inhibitors, retrojusticidin B and phyllamyricin A, were prepare

Transformations of lignans, Part V. Reactions of DDQ with a gmelinol hydrogenolysis product and its derivatives

Hydrogenolysis of gmelinol 8 with sodium in liquid ammonia gives a triol 9, which is converted under various reaction conditions into a range of derivatives including the di- and tri-O-methyl ethers 10 and 11, a 3,4- dibenzyl-3-hydroxy-tetrahydrofuran 12, and its acetate 13. These derivatives undergo oxidative cyclisation with DDQ in acetic acid or trifluoroacetic acid to yield 1-aryltetralin, 1-arylnaphthalene, dibenzocyclooctadiene and spirodienone derivatives in reactions which provide biomimetic analogies for biogenetic transformations of lignans.

Oxidative aryl-aryl, aryl-benzyl coupling of lignans-reactions of phyllanthin and haloderivatives with TTFA, DDQ, Li/THF)))): Synthesis of dibenzocyclooctadiene system and phyltetralin

Treatment of phyllanthin (1) with TTFA in TFA gives dibenzocyclooctadiene (2) and phyltetralin (3). Treatment of (1) with DDQ in TFA also affords (2) while with DDQ in acetic acid gives 1-phenylnaphthalenic lignan (4). Synthesis of halophyllanthins (5,6,7) and its Ullmann reaction in ultrasonic condition affords reductive dehalogenated product (1) instead of (2). Treatment of (1) with POCl3 in TCA gives (+) 3,4-diveratryltetrahydrofuran (8) and its conversion to (9) also reported. Treatment of (5) with TTFA/TFA gives (9).

REACTIONS OF ARYLTETRALIN LIGNANS WITH DDQ - AN EXAMPLE OF DDQ OXIDATION OF AN ALLYLIC ETHER GROUP.

The reactions of lintetralin, phyltetralin, nirtetralin and hypophyllanthin with DDQ yield in each case two products which have been identified as an arylnaphthalene aldehyde and its dihydro derivative.