[Total synthesis of nordihydroguaiaretic acid].
beta-Keto ester(5) was obtained from vanilin through etherification, oxidation and condensation with acetoacetic ester, (5) on oxidative coupling reaction by NaOEt/I2 produced dimer (6) in high yield. Acid catalyzed cyclodehydration of (6) gave the furan derivative(7), and by a series of selective hydrogenation nordihydroguaiaretic acid, furoguaiacin dimethyl ether and dihydroguaiaretic acid dimethyl ether were synthesized.
Wu
A X
AX
Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000.
Zhao
Y R
YR
Chen
N
N
Pan
X F
XF
D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry; D009637:Masoprocol / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry
D005663:Furans; D017705:Lignans; C437398:furoguaiacin dimethyl ether; C015816:dihydroguaiaretic acid; D006139:Guaiacol; D009637:Masoprocol