High yield total syntheses of XH-14 derivatives using Sonogashira coupling reaction

被引:19
作者
Bang, Hyun Bae
Han, Su Young
Choi, Da Hye
Hwang, Jung Woon
Jun, Jong-Gab [1 ]
机构
[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea
关键词
XH-14; benzo[b]furan; Colvin rearrangement; Sonogashira coupling; iodocyclization; ADENOSINE-A1-RECEPTOR LIGAND; STRUCTURE ELUCIDATION; ADENOSINE RECEPTORS; BENZOFURAN;
D O I
10.3998/ark.5550190.0010.212
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A high yielding synthetic route to XH-14 derivatives is described using a Sonogashira reaction as a key step. Introduction of iodine into the structure and optimization of the synthetic sequence were essential for the successful syntheses of XH-14 derivatives. The nine-step reaction sequence gave 2 and 3 in 30% and 55% overall yields, respectively.
引用
收藏
页码:112 / 125
页数:14
相关论文
共 19 条
[1]   Facile Total Synthesis of Benzo[b]furan Natural Product XH-14 [J].
Bang, Hyun Bae ;
Han, Su Young ;
Choi, Da Hye ;
Yang, Deok Mo ;
Hwang, Jung Woon ;
Lee, Hyun Suck ;
Jun, Jong-Gab .
SYNTHETIC COMMUNICATIONS, 2009, 39 (03) :506-515
[2]   STRUCTURE ELUCIDATION AND TOTAL SYNTHESIS OF NEW TANSHINONES ISOLATED FROM SALVIA-MILTIORRHIZA BUNGE (DANSHEN) [J].
CHANG, HM ;
CHENG, KP ;
CHOANG, TF ;
CHOW, HF ;
CHUI, KY ;
HON, PM ;
TAN, FWL ;
YANG, Y ;
ZHONG, ZP ;
LEE, CM ;
SHAM, HL ;
CHAN, CF ;
CUI, YX ;
WONG, HNC .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3537-3543
[3]   INHIBITION OF RADIOLIGAND BINDING TO A1 ADENOSINE RECEPTORS BY BAY-K8644 AND NIFEDIPINE [J].
CHEUNG, WT ;
SHI, MM ;
YOUNG, JD ;
LEE, CM .
BIOCHEMICAL PHARMACOLOGY, 1987, 36 (13) :2183-2186
[4]  
Choi DH, 2008, B KOREAN CHEM SOC, V29, P1594
[5]   SIMPLE PROCEDURE FOR ELABORATION OF CARBONYL-COMPOUNDS INTO HOMOLOGOUS ALKYNES [J].
COLVIN, EW ;
HAMILL, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :869-874
[6]  
Dean F. M., 1973, TOTAL SYNTHESIS NATU, V1, P467
[7]   Comparison of iodination of methoxylated benzaldehydes and related compounds using iodine/silver nitrate and iodine/periodic acid [J].
Hathaway, Bruce A. ;
White, Kristen L. ;
McGill, Mark E. .
SYNTHETIC COMMUNICATIONS, 2007, 37 (19-21) :3855-3860
[8]   A new synthesis of the benzofuran adenosine antagonist XH-14 [J].
Hutchinson, SA ;
Luetjens, H ;
Scammells, PJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (24) :3081-3084
[9]   ADENOSINE RECEPTORS - PHARMACOLOGY, STRUCTURE-ACTIVITY-RELATIONSHIPS, AND THERAPEUTIC POTENTIAL [J].
JACOBSON, KA ;
VANGALEN, PJM ;
WILLIAMS, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (03) :407-422
[10]   A novel strategy for the synthesis of benzofuran skeleton neolignans: Application to ailanthoidol, XH-14, and obovaten [J].
Kao, CL ;
Chern, JW .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19) :6772-6787