Self-sensitized photooxygenation of 3,4-dialkoxyfurans to vitamin C or its derivatives.
Self-sensitized photooxygenation of 3,4-dialkoxyfurans 3a-d with molecular oxygen and UV- or sunlight at room temperature gave vitamin C derivatives 2a-d in good to excellent yields. Furan 3c, having photodegradable protecting groups, was also photooxygenated to give L-ascorbic acid (1) in a "one-pot" reaction. Furthermore, a novel photolytic transformation was developed for deuteration of furan 3b at the C-2 position with D(2)O to give furan 3d in 95% yield. Toxicity of furans 3a-c and butenolides 2a-c against human embryonic cell, murine embryo fibroblasts, normal fibroblasts, HeLa, and Vero cell lines in the presence of oxygen and indirect solar light was found to be much less than those of the antipsoriasis drugs anthralin and 8-methoxypsoralen.
Hakimelahi
G H
GH
Institute of Chemistry, Academia Sinica, Taipei, Taiwan 115, Republic of China. hosein@chem.sinica.edu.tw
Jain
M L
ML
Ly
T W
TW
Chen
I C
IC
Ethiraj
K S
KS
Hwu
J R
JR
Moshfegh
A A
AA
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001205:Ascorbic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line / Q000187:drug effects / Q000528:radiation effects; D002522:Chlorocebus aethiops; D005663:Furans / Q000737:chemistry* / Q000528:radiation effects; D006367:HeLa Cells / Q000187:drug effects / Q000528:radiation effects; D006801:Humans; D051379:Mice; D010084:Oxidation-Reduction; D010100:Oxygen / Q000378:metabolism; D010777:Photochemistry; D014466:Ultraviolet Rays; D014709:Vero Cells / Q000187:drug effects / Q000528:radiation effects
D000975:Antioxidants; D005663:Furans; D001205:Ascorbic Acid; D010100:Oxygen