Synthesis of 3′H-spiro[cyclohexane-1,1′-isobenzofuran]-2,5-dien-4-one and Skeleton construction of a type D spirobisnaphthalene structure via dearomatization by a high-valence iodine reagent and Diels-Alder reaction

被引：0

作者：

Ma, Haoyun ^{[1
]}

An, Xinkun ^{[1
]}

Zhang, Tingting ^{[1
]}

He, Xie ^{[1
]}

Li, Yiyi ^{[1
]}

Wang, Mingan ^{[1
]}

机构：

[1] China Agr Univ, Coll Sci, Innovat Ctr Pesticide Res, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2024年 / 48卷 / 36期

基金：

中国国家自然科学基金;

关键词：

PHENOL DEAROMATIZATION; C-C;

D O I：

10.1039/d4nj03285c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The core skeleton syntheses of 3 ' H-spiro[cyclohexane-1,1 '-isobenzofuran]-2,5-dien-4-one, and their derivatives (3a-3w) of spirobisnaphthalene urnucratins, plecmillins, and lignan kadsulignan, were explored using Suzuki-Miyaura coupling product biphenols as the precursors and intramolecular oxidative dearomatization with high-valence iodine reagent PIFA as the key step in 46-91% yields. A wide range of functional groups were tolerated. Then, using this strategy in combination with the Diels-Alder reaction, two skeleton molecules (5ah and 6d) of the natural products urnucratins and plecmillins were successfully constructed in 78% and 39% overall yields, which provides a potential methodology for the total synthesis of Type D spirobisnaphthalene urnucratins and other natural products with similar structures.

引用

页码：15846 / 15855

页数：10