Versatile and expeditious synthesis of aurones via AuI-catalyzed cyclization

Versatile and expeditious synthesis of aurones via AuI-catalyzed cyclization
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DOI:
10.1021/jo702197b
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发表时间:
2008-02-15
影响因子:
3.6
通讯作者:
Pale, Patrick
Pale, Patrick
中科院分区:
化学2区
文献类型:
--
作者:
Harkat, Hassina;Blanc, Aurelien;Pale, Patrick

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橙酮可以方便地在三步程序中形成,包括金(I)催化的2-(1-羟基丙-2-炔基)苯酚环化作为高度区域和立体选择性的关键步骤。从取代的水杨醛开始可以获得多种多样的衍生物。合成了天然产物4,6,3 ',4'-四甲氧基橙酮,并对两个天然产物(dalmaisione D和4 '-氯橙酮)进行了结构修正。
[GRAPHICS]Aurones are conveniently formed in a three-step procedure including a gold(I)-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3',4'-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4'-chloroaurone) were achieved.