由抗坏血酸生成2-羟基-4-羟甲基-3-(吲哚-3-基)环戊-2-烯酮衍生物。

The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)-cyclopent-2-enone derivatives from ascorbigens.

作者信息

Korolev A M, Yudina L N, Rozhkov I I, Lysenkova L N, Lazhko E I, Luzikov Y N, Preobrazhenskaya M N

机构信息

Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow.

出版信息

Carbohydr Res. 2001 Feb 28;330(4):469-77. doi: 10.1016/s0008-6215(00)00310-4.

DOI:10.1016/s0008-6215(00)00310-4

PMID:11269398

Abstract

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.

摘要

本文描述了一种简便的制备方法，通过抗坏血酸原或其N-衍生物在L-抗坏血酸的温热溶液中经连续多米诺反应降解，以15 - 40%的产率制备3-(吲哚-3-基)-2-羟基-4-羟甲基环戊-2-烯酮及其N-衍生物。通过(N-烷基吲哚-3-基)乙醇酸与抗坏血酸缩合，以30 - 40%的产率得到相同的环戊烯酮衍生物。2,6-二羟基-1-(吲哚-3-基)己-1,4-二烯-3-酮和2-羟基-4-羟甲基-5-(吲哚-3-基)环戊-2-烯酮被鉴定为该反应的中间体。