Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2-Vinylphenol: Synthesis of Indeno[2,1-c]chromenes

被引：5
作者：
Zhang, Xiang-Zhi [1 ]
Zhu, Zhi-Qiang [1 ]
Wu, Teng-Fei [1 ]
Pan, Han-Peng [1 ]
Peng, Jin-Bao [1 ]
Ma, Ai-Jun [1 ]
机构：
[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Guangdong, Peoples R China
来源：
ORGANIC LETTERS | 2023年
关键词：
CAESALPINIA-SAPPAN; FORMAL SYNTHESIS; BRAZILIN; (+/-)-BRAZILIN; 1,8-ADDITION; CONSTRUCTION; CYCLIZATION; APOPTOSIS;
D O I：
10.1021/acs.orglett.3c00179
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual structural reconstruction of 2-vinylphenol, involving cleavage of the C1 '=C2 ' bond and formation of four new bonds. This method provides a convenient and mild approach to generate synthetically important functionalized indeno[2,1-c]chromenes. The mechanism of the reaction is proposed from several control experiments.
引用
收藏
页码：1299 / 1304
页数：6
相关论文
共 50 条
[11]   Enantioselective syntheses of (+)- and (-)-brazilin [J].
Javed, Umair ;
Karim, Moinul ;
Jahng, Katherine C. ;
Park, Jae-Gyu ;
Jahng, Yurngdong .
TETRAHEDRON-ASYMMETRY, 2014, 25 (18-19) :1270-1274
[12]   Palladium-Catalyzed Asymmetric (4+2) Annulation of γ-Methylidene-δ-valerolactones with Alkenes: Enantioselective Synthesis of Functionalized Chiral Cyclohexyl Spirooxindoles [J].
Jia, Zhi-Long ;
An, Xian-Tao ;
Deng, Yu-Hua ;
Pang, Lin-Han ;
Liu, Chun-Fang ;
Meng, Le-Le ;
Xue, Jia-Kun ;
Zhao, Xian-He ;
Fan, Chun-An .
ORGANIC LETTERS, 2021, 23 (03) :745-750
[13]   Palladium-Catalyzed Asymmetric (2+3) Annulation of p-Quinone Methides with Trimethylenemethanes: Enantioselective Synthesis of Functionalized Chiral Spirocyclopentyl p-Dienones [J].
Jia, Zhi-Long ;
An, Xian-Tao ;
Deng, Yu-Hua ;
Wang, Hui-Bin ;
Gan, Kang-Ji ;
Zhang, Jing ;
Zhao, Xian-He ;
Fan, Chun-An .
ORGANIC LETTERS, 2020, 22 (11) :4171-4175
[14]   A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation [J].
Jung, Youngeun ;
Kim, Ikyon .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) :4331-4335
[15]   Total Synthesis of Brazilin [J].
Jung, Youngeun ;
Kim, Ikyon .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) :2001-2005
[16]   Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane [J].
Kim, Jinwoo ;
Kim, Ikyon .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (01) :89-100
[17]   Brazilin Inhibits Growth and Induces Apoptosis in Human Glioblastoma Cells [J].
Lee, Dae-Young ;
Lee, Mi-Kyoung ;
Kim, Geum-Soog ;
Noh, Hyung-Jun ;
Lee, Min-Ho .
MOLECULES, 2013, 18 (02) :2449-2457
[18]   Pestalachlorides A-C, antifungal metabolites from the plant endophytic fungus Pestalotiopsis adusta [J].
Li, Erwei ;
Jiang, Lihua ;
Guo, Liangdong ;
Zhang, Hua ;
Che, Yongsheng .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (17) :7894-7899
[19]   Organocatalytic site- and stereoselective 1,6-additions of N-aryl-3-oxobutanamides to propargylic aza-p-quinone methides [J].
Li, Fushuai ;
Chen, Xuling ;
Liang, Shuai ;
Shi, Zhenyan ;
Li, Pengfei ;
Li, Wenjun .
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (21) :3446-3451
[20]   Total synthesis of (±)-brazilin and formal synthesis of (±)-brazilein, (±)-brazilide A using m-CPBA [J].
Li, Liang-Qun ;
Li, Ming-Ming ;
Wang, Kou ;
Qin, Hong-Bo .
TETRAHEDRON LETTERS, 2013, 54 (45) :6029-6031
12345