41328-89-6

Upstream product

• 10569-14-9 Dihydrogmelinol 
• 33464-73-2 (-)-O-methyltrachelogenine 
• 469-28-3 (+)-1-hydroxy-6-epipinoresinol 4',4''-di-O-methyl ether 

Downstream Products

• 252750-94-0 (2S,3S)-1,4-Bis-(3,4-dimethoxy-phenyl)-2,3-bis-methoxymethyl-butan-2-ol 
• 252750-96-2 C₂₅H₃₆O₇ 
• 252751-08-9 Acetic acid (3aS,9S,9aS)-9-(3,4-dimethoxy-phenyl)-4-hydroxy-6,7-dimethoxy-1,4,9,9a-tetrahydro-naphtho[2,3-c]furan-3a-yl ester 
• 252751-03-4 Acetic acid (3aS,9S,9aS)-9-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-1,4,9,9a-tetrahydro-naphtho[2,3-c]furan-3a-yl ester 
• 252751-02-3 (3aS,9S,9aS)-9-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-1,4,9,9a-tetrahydro-naphtho[2,3-c]furan-3a-ol 
• 252750-99-5 Acetic acid (3S,4S)-3,4-bis-(3,4-dimethoxy-benzyl)-tetrahydro-furan-3-yl ester 
• 252750-98-4 (3S,4S)-3,4-Bis-(3,4-dimethoxy-benzyl)-tetrahydro-furan-3-ol 

Relevant academic research and scientific papers

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.