Novel oxidative phenol-coupling reaction with phosphomolybdic acid on silica gel support: Regioselective biomimetic synthesis of dimeric phenanthrene derivatives
作者:P.L. Majumder、Mausumi Basak
DOI:10.1016/s0040-4020(01)82403-0
日期:1991.9
Biomimetic synthesis of the naturally occurring dimeric phenanthrene derivatives, cirrhopetalanthrin (3a) and flavanthrin (7a), and their structural analogues 3c, 3e, 5a and 7c was achieved in very high yields by regioselective oxidative coupling of their respective phenolic monomers 2a, 6a, 2c, 2e, 4a and 6c with phosphomolybdic acid on a silica gel support. Unlike coelonin (6a) and lusianthridin
天然存在的二聚体菲衍生物,cirrhopetalanthrin(仿生合成图3a)和flavanthrin(7A),和它们的结构类似物图3c,图3e,图5a和图7c是在非常高的产率通过区域选择性氧化来实现它们各自的酚单体的联接图2a,6a中,2c,2e,4a和6c以及在硅胶载体上的磷钼酸。不同于腔肠素(6a)和芦硫苷(6c),2,7-二羟基-3,4,6-三甲氧基-9,10-二氢菲(6e)在相似的氧化作用下,得到菲二聚体3e。代替了预期的9,10-二氢菲二聚体7e。β-萘酚几乎可以定量得到相应的1,1'-二聚体1a。从化合物及其各自的乙酰基衍生物的各种光谱数据确定了新的二聚化合物的结构。