The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)-cyclopent-2-enone derivatives from ascorbigens.
A facile preparation is described of 3-(indol-3-yl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone and its N-derivatives in 15-40% yields by the degradation of ascorbigen or its N-derivatives in a warm solution of L-ascorbic acid through a sequential domino reaction. The same cyclopentenone derivatives were obtained in 30-40% yields by the condensation of (N-alkylindol-3-yl)glycolic acids with ascorbic acid. 2,6-Dihydroxy-1-(indol-3-yl)hexa-1,4-diene-3-one and 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone were identified as intermediates in this reaction.
Korolev
A M
AM
Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow.
Yudina
L N
LN
Rozhkov
I I
II
Lysenkova
L N
LN
Lazhko
E I
EI
Luzikov
Y N
YN
Preobrazhenskaya
M N
MN
D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D003517:Cyclopentanes / Q000138:chemical synthesis*; D006358:Hot Temperature; D006868:Hydrolysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D003517:Cyclopentanes; D007211:Indoles; C053152:ascorbigen; D001205:Ascorbic Acid