124281-57-8

Upstream product

• 469-28-3 (+)-1-hydroxy-6-epipinoresinol 4',4''-di-O-methyl ether 
• 469-28-3 gmelinol 

Downstream Products

• 124281-62-5 C₂₇H₃₄O₈ 
• 124281-61-4 [(4aR,10R,10aR)-10-(3,4-Dimethoxy-phenyl)-7,8-dimethoxy-2,2-dimethyl-4,4a,5,10-tetrahydro-naphtho[2,3-d][1,3]dioxin-10a-yl]-methanol 
• 124281-60-3 C₂₅H₃₂O₇ 
• 124281-59-0 Acetic acid (1R,2R,3R)-3-acetoxymethyl-1-(3,4-dimethoxy-phenyl)-2-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl ester 

Relevant academic research and scientific papers

Synthetic experiments in lignans Part XV - Reductive rearrangements of 2,6-diaryl-3,7-dioxabicycloocatne lignans with AlCl3 and (C2H5)3SiH

The mixture of AlCl3 and (C2H5)3SiH has been found to cleave the benzyl ethers of the lignans, gmelinol, paulownin, wodeshiol and eudesmin leading to a tetrahydrofuran, a tetrahdyropyran or an aryltetralin derivative by reductive rearrangement.

REACTION OF GMELINOL WITH TRIETHYLSILANE AND BF3-ETHERATE - REARRANGEMENT OF THE 2,6-DIARYL-3,7-DIOXABICYCLOOCTANE SKELETON

Reaction of gmelinol 1 with triethylsilane and BF3-etherate gave two products, the major product 2 being an isomer of cycloolivil dimethyl ether, formed by reductive rearrangement of the 2,6-diaryl-3,7-dioxabicyclooctane skeleton.The minor product