Journal of the American Chemical Society p. 5926 - 5927 (2002)
Update date:2022-08-17
Topics:
Hansen, Chad A.
Frost
New synthetic connections have been established between glucose and aromatic chemicals such as pyrogallol, hydroquinone, and resorcinol. The centerpiece of this approach is the removal of one oxygen atom from 1,2,3,4-tetrahydroxybenzene, hydroxyhydroquinone, and phloroglucinol methyl ether to form pyrogallol, hydroquinone, and resorcinol, respectively. Deoxygenations are accomplished by Rh-catalyzed hydrogenation of the starting polyhydroxybenzenes followed by acid-catalyzed dehydration of putative dihydro intermediates. Pyrogallol synthesis consists of converting glucose into myo-inositol, oxidation to myo-2-inosose, dehydration to 1,2,3,4-tetrahydroxybenzene, and deoxygenation to form pyrogallol. Synthesis of pyrogallol via myo-2-inosose requires 4 enzyme-catalyzed and 2 chemical steps. For comparison, synthesis of pyrogallol from glucose via gallic acid intermediacy and the shikimate pathway requires at least 20 enzyme-catalyzed steps. A new benzene-free synthesis of hydroquinone employs conversion of glucose into 2-deoxy-scyllo-inosose, dehydration of this inosose to hydroxyhydroquinone, and subsequent deoxygenation to form hydroquinone. Synthesis of hydroquinone via 2-deoxy-scyllo-inosose requires 2 enzyme-catalyzed and 2 chemical steps. By contrast, synthesis of hydroquinone using the shikimate pathway and intermediacy of quinic acid requires 18 enzyme-catalyzed steps and 1 chemical step. Methylation of triacetic acid lactone, cyclization, and regioselective deoxygenation of phloroglucinol methyl ether affords resorcinol. Given the ability to synthesize triacetic acid lactone from glucose, this constitutes the first benzene-free route for the synthesis of resorcinol. Copyright
View MoreHuaihua Baohua Biotechnology Co.,Ltd
website:http://www.baochengchem.com
Contact:86-519-82698291
Address:HouYang chemical development zone,Jintan,Jiangsu,China (213200)
Nanjing Xi Ze Biological Technology Co., Ltd
Contact:86-025-66023220
Address:Address: Nanjin Qixia District Maigaoqiao R & D base in Pioneer Park Chun Yin Road 18-A928
website:http://www.hybio.com.cn
Contact:+86 755 26588093
Address:No.9 Linkong West Street, Hengdian Street, Huangpi District, Wuhan City, China.
Jiaxing Trustworthy Import And Export Co.,Ltd
Contact:+86-573-82030555
Address:Room 1202, Unit B, Charming plaza,No.1558 East Zhongshan Road , Jiaxing City, Zhejiang Province, China.
jiangsu senxuan pharmaceutical and chemical co.,ltd
Contact:86-523-87982810
Address:hongqiao industrial zone,taixing,jiangsu china
Doi:10.1021/j100117a018
(1993)Doi:10.1002/jlcr.2580150147
(1978)Doi:10.1055/s-0035-1561268
(2016)Doi:10.1021/ja00384a048
(1982)Doi:10.1246/bcsj.48.3278
(1975)Doi:10.1002/etc.5620210606
(1874)