70574-33-3

Upstream product

• 100-66-3 methoxybenzene 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 32097-05-5 4-methoxy-β,β-dimethylacrylophenone 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 70574-34-4 1-(4-methoxyphenyl)-5-methylcyclohexa-1,4-diene 
• 70574-35-5 (+/-)-3-methoxy-6,6-dimethyl-B-norestra-1,3,5⁽¹⁰⁾,8,14-pentaen-17-one 
• 81226-69-9 4b,5,6,7a,8,8a,9,11-octahydro-4b-hydroxy-7-keto-3-methoxy-9-(5-methoxy-3,3-dimethylindanyl)-7a,11,11-trimethyldibenzazulene 

Relevant academic research and scientific papers

Total Synthesis of Substituted (+/-)-6,6-Dimethyl-B-norestra-1,3,5(10)-trien-17β-ols and their 9β-Isomers

Total syntheses of (+/-)-1,4-dimethoxy-6,6-dimethyl-B-norestra-1,3,5(10)-trien-17β-ol (11a), (+/-)-2,3-dimethoxy-6,6-dimethyl-B-norestra-1,3,5(10)-trien-17β-ol (11b), and (+/-)-3-methoxy-6,6-dimethyl-B-norestra-1,3,5(10)-trien-17β-ol (11c), have been carried out starting from 4,7-dimethoxy-3,3-dimethylindan-1-one (1), 5,6-dimethoxy-3,3-dimethylindan-1-one (2), and 4'-methoxy-3-methylbut-2-enophenone (4), respectively.Generally, it is found that the intermediate 6,6-dimethyl-B-norestra-1,3,5(10),8-tetraen-17β-ols (10), on lithium-liquid ammonia reduction, yield a mixture of 8β,9α- and 8β,9β-trienols, (11) and (12) respectively, in the ratio 1 : 1.This is due to the comparable stabilities of these two isomers.However, the reaction carried out in presence of aniline affords a higher percentage of the 8β,9α-trienol (11).The assignment of configurations is made by chemical and 1H n.m.r. analysis.Catalytic hydrogenation of the tetraenols (10) is shown to proceed via initial isomerisation to the corresponding 6,6-dimethyl-B-norestra-1,3,5(10),9(11)-tetraen-17β-ols (26), followed by hydrogenation from the β-side to give, exclusively, the 8β,9β-trienols (12).