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

[21] Asymmetric Total Synthesis of Propindilactone G, Part 2: Enantioselective Construction of the Fully Functionalized BCDE Ring System
Zhang, Jia-Jun
You, Lin
Wang, Yue-Fan
Li, Yuan-He
Liang, Xin-Ting
Zhang, Bo
Yang, Shou-Liang
Su, Qi
Chen, Jia-Hua
Yang, Zhen
CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (09) : 1414 - 1424
[22] Enantioselective total synthesis and absolute configuration of the natural norsesquiterpene 7-demethyl-2-methoxycalamenene by a silane-terminated intramolecular Heck reaction
Tietze, LF
Raschke, T
LIEBIGS ANNALEN, 1996, (12): : 1981 - 1987
[23] TOTAL SYNTHESIS OF (+/-)-BETA-BULNESENE VIA INTRAMOLECULAR CYCLO-ADDITION OF A 2-SUBSTITUTED 3-OXIDOPYRYLIUM
BROMIDGE, SM
SAMMES, PG
STREET, LJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08): : 1725 - 1730
[24] Enantioselective synthesis of 2-substituted pyrrolidines via domino cross metathesis/intramolecular aza-Michael addition
Liu, Hanbin
Zeng, Chuanqi
Guo, Jiajia
Zhang, Mengyao
Yu, Shouyun
RSC ADVANCES, 2013, 3 (06): : 1666 - 1668
[25] Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4+2] benzannulation:: Enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2
Sato, K
Asao, N
Yamamoto, Y
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22): : 8977 - 8981
[26] Construction of 4a,8a-cis-octahydroquinolin-7-one core using an intramolecular aldol type of cyclization:: An application to enantioselective total synthesis of lepadin B
Toyooka, N
Okumura, M
Takahata, H
Nemoto, H
TETRAHEDRON, 1999, 55 (35) : 10673 - 10684
[27] Highly stereoselective construction of 4,6-cis-substituted quinolizidine ring core:: An application to enantioselective total synthesis of the marine alkaloid clavepictines A, B and pictamine
Toyooka, N
Yotsui, Y
Yoshida, Y
Momose, T
Nemoto, H
TETRAHEDRON, 1999, 55 (52) : 15209 - 15224
[28] Synthesis of Thieno[3,2-b]benzofurans by Palladium-catalyzed Intramolecular C-H/C-H Coupling
Kaida, Hiroyuki
Satoh, Tetsuya
Hirano, Koji
Miura, Masahiro
CHEMISTRY LETTERS, 2015, 44 (08) : 1125 - 1127
[29] Design, synthesis and antitubercular evaluation of novel 2-substituted-3H-benzofuro benzofurans via palladium-copper catalysed Sonagashira coupling reaction
Yempala, Thirumal
Sridevi, Jonnalagadda Padma
Yogeeswari, Perumal
Sriram, Darmarajan
Kantevari, Srinivas
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (19) : 5393 - 5396
[30] Synthesis of Spirolactones and Functionalized Benzofurans via Addition of 3-Sulfonylphthalides to 2-Formylaryl Triflates and Conversion to Benzofuroisocoumarins
Nair, Deepa
Basu, Pallabita
Pati, Soumyaranjan
Baseshankar, Kajal
Sankara, Chenikkayala Siva
Namboothiri, Irishi N. N.
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07): : 4519 - 4527

← 1 2 3 4 5 →