OLIGOMERIC FLAVANOIDS .15. BASE-CATALYZED PYRAN REARRANGEMENTS OF PROCYANIDIN B-2, AND EVIDENCE FOR THE OXIDATIVE TRANSFORMATION OF B-TO A-TYPE PROCYANIDINS

OLIGOMERIC FLAVANOIDS .15. BASE-CATALYZED PYRAN REARRANGEMENTS OF PROCYANIDIN B-2, AND EVIDENCE FOR THE OXIDATIVE TRANSFORMATION OF B-TO A-TYPE PROCYANIDINS
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DOI:
10.1016/s0040-4020(01)87771-1
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发表时间:
1990-01-01
期刊:
影响因子:
2.1
通讯作者:
FERREIRA, D
FERREIRA, D
中科院分区:
化学3区
文献类型:
--
作者:
BURGER, JFW;KOLODZIEJ, H;FERREIRA, D

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原花青素B-2 - 3在0.1 M NaHCO 2溶液中进行容易的C-环异构化,形成一系列新的3,4,9,10-四氢-2H,8H-吡喃并[2,3-h]色烯7、9和10。B-至A-型原花青素2的低转化百分比根据在C-2(C-环)处的杂化离子的初始氧化去除而合理化。
Procyanidin B-2 3 is subject to facile C-ring isomerizations in 0.1 M NaHCO2 solution to form a novel series of 3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-h]chromenes 7, 9, and 10. The low percentage conversion of B- to A-type procyanidine 2 is rationalized in terms of an initial oxidative removal of hybride ion at C-2 (C-ring).