Construction of 2-Substituted-3-Functionalized Benzofurans via Intramolecular Heck Coupling: Application to Enantioselective Total Synthesis of Daphnodorin B

被引：69

作者：

Yuan, Hu ^{[1
,2
]}

Bi, Kai-Jian ^{[1
]}

Li, Bo ^{[1
]}

Yue, Rong-Cai ^{[1
]}

Ye, Ji ^{[1
]}

Shen, Yun-Heng ^{[1
]}

Shan, Lei ^{[1
]}

Jin, Hui-Zi ^{[2
]}

Sun, Qing-Yan ^{[3
]}

Zhang, Wei-Dong ^{[1
,2
]}

机构：

[1] Second Mil Med Univ, Sch Pharm, Dept Phytochem, Shanghai 200433, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai 200240, Peoples R China

[3] Second Mil Med Univ, Sch Pharm, Dept Organ Chem, Shanghai 200433, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 18期

关键词：

FUNCTIONALIZED BENZOFURANS; CARBONYLATIVE ANNULATION; COMBINATORIAL SYNTHESIS; EFFICIENT; FLAVANS; ACYLPHENYLCARBONATES; 12-LIPOXYGENASE; CONSTITUENTS; ACYLPHENOLS; CYCLIZATION;

D O I：

10.1021/ol4021095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach was developed for the synthesis of 2-substituted-3-functionalized benzofurans, using an intramolecular Heck reaction which was further applied in the first enantioselective total synthesis of Daphnodorin B.

引用

页码：4742 / 4745

页数：4

共 50 条

[31] Convenient synthesis of substituted 3-alkenylpyrazolo[1,5-α]pyrimidines via Heck cross-coupling reaction
Yin, LX
Liebscher, E
SYNTHESIS-STUTTGART, 2004, (14): : 2329 - 2334
[32] Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition
Cheng, Shuanghua
Yu, Shouyun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (43) : 8607 - 8610
[33] Organocatalytic, Enantioselective Synthesis of 1-and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole
Ravindra, Barnala
Maity, Sanjay
Das, Braja Gopal
Ghorai, Prasanta
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (14): : 7008 - 7018
[34] A stereoselective synthesis of 3-substituted hexahydroindeno[2,1-b]pyrroles via an intramolecular azomethine ylide cycloaddition
Harling, JD
Orlek, BS
TETRAHEDRON, 1998, 54 (49) : 14905 - 14912
[35] Asymmetric cyclization via oxygen cation radical:: Enantioselective synthesis of cis-4b,9b-dihydrobenzofuro[3,2-b]benzofurans
Masutani, K
Irie, R
Katsuki, T
CHEMISTRY LETTERS, 2002, (01) : 36 - 37
[36] An alternate method for the synthesis of 2-aryl/alkyl-5-bromo-7-methoxy benzofurans; application to the synthesis of Egonol, Homoegonol, and analogs via Heck reaction
More, Kishor R.
Mali, R. S.
TETRAHEDRON, 2016, 72 (47) : 7496 - 7504
[37] Synthesis of Alkaloid (-)-205B via Stereoselective Reductive Cross-Coupling and Intramolecular [3+2] Cycloaddition
Yang, Dexi
Micalizio, Glenn C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (37) : 15237 - 15240
[38] Synthesis of 3-Substituted Isocoumarins via a Cascade Intramolecular Ullmann-Type Coupling-Rearrangement Process
Ge, Zhi-Yuan
Fei, Xiang-Dong
Tang, Ting
Zhu, Yong-Ming
Shen, Jing-Kang
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (13): : 5736 - 5743
[39] Enantioselective synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters: application to the total synthesis of (+)-alexine
Yu, Lu
Somfai, Peter
RSC ADVANCES, 2019, 9 (05) : 2799 - 2802
[40] Copper-Catalyzed Double Intramolecular Ullmann Coupling for the Synthesis of Diastereomerically and Enantiomerically Pure 4b,9b-Dihydrobenzofuro[3,2-b]benzofurans
Imrich, Hans-Georg
Conrad, Juergen
Beifuss, Uwe
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (35) : 7718 - 7734

← 1 2 3 4 5 →