Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of a 2-Arylbenzofuran Skeleton: Total Synthesis of Cuspidan B

被引：17
作者：
Nambu, Hisanori [1 ]
Ono, Naoki [1 ]
Yakura, Takayuki [1 ]
机构：
[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Toyama 9300194, Japan
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 12期
基金：
日本学术振兴会;
关键词：
cyclopropanes; benzofurans; natural products; ring opening; cyclization; total synthesis; ONE-POT SYNTHESIS; DONOR-ACCEPTOR CYCLOPROPANES; C-H INSERTION; ANNULATION/CROSS-COUPLING STRATEGY; 3+2 CROSS-CYCLOADDITIONS; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; BROMODIMETHYLSULFONIUM BROMIDE; SUBSTITUTED CYCLOPROPANES; DIAZODICARBONYL COMPOUNDS;
D O I：
10.1055/s-0035-1561590
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Acid-catalyzed ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes under metal-free conditions proceeded smoothly at room temperature to provide 2-aryl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-ones in excellent yields without the formation of 3-substituted isomers. The obtained product was converted into a 2-arylbenzofuran derivative via a synthetically useful 2-aryl-2,3-dihydrobenzofuran intermediate. Furthermore, the first total synthesis of cuspidan B was achieved by using the present method.
引用
收藏
页码：1892 / 1901
页数：10
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