An efficient synthesis of the indole acetic acid metabolite of MK-0462

被引：15

作者：

Chen, CY ^{[1
]}

Lieberman, DR ^{[1
]}

Street, LJ ^{[1
]}

Guiblin, AR ^{[1
]}

Larsen, RD ^{[1
]}

Verhoeven, TR ^{[1
]}

机构：

[1] MERCK SHARP & DOHME LTD, RES LABS, HARLOW CM20 2QR, ESSEX, ENGLAND

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 10期

关键词：

D O I：

10.1080/00397919608003552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed coupling of iodoaniline 2 with bis-TES propargyl alcohol 3 gives indole-3-methanol 4b in 72% yield. Displacement of the hydroxy group of 4b by sodium cyanide followed by hydrolysis of the cyano group and desilylation provides the indole acetic acid metabolite, L-749,335 (1), of the 5-HT1D receptor agonist MK-0462.

引用

页码：1977 / 1984

页数：8

共 50 条

[41] Cocrystals of indole-3-acetic acid and indole-3-butyric acid: Synthesis, structural characterization and Hirshfeld surface analysis
Abidi, Syed Sibte Asghar
Azim, Yasser
Gupta, Abhishek Kumar
Pradeep, Chullikkattil P.
JOURNAL OF MOLECULAR STRUCTURE, 2018, 1166 : 202 - 213
[42] INTERRELATIONSHIP OF INDOLE-3-ACETIC ACID CATECHIN AND INDOLE-3-ACETIC ACID OXIDASE IN IMMATTURE PEACH SEEDS
RITZERT, RW
SELL, HM
BUKOVAC, MJ
PLANT PHYSIOLOGY, 1965, S 40 : R8 - &
[43] An efficient biocatalytic synthesis of imidazole-4-acetic acid
Zhao, Weirui
Ding, Huanru
Hu, Sheng
Huang, Jun
Lv, Changjiang
Mei, Jiaqi
Jin, Zhihua
Yao, Shanjing
Mei, Lehe
BIOTECHNOLOGY LETTERS, 2018, 40 (07) : 1049 - 1055
[44] SYNTHESIS OF THE PHYTOHORMONE INDOLE-3-ACETIC-ACID BY RHIZOSPHERE BACTERIA OF THE GENUS PSEUDOMONAS
MORDUKHOVA, EA
SKVORTSOVA, NP
KOCHETKOV, VV
DUBEIKOVSKII, AN
BORONIN, AM
MICROBIOLOGY, 1991, 60 (03) : 345 - 349
[45] An efficient biocatalytic synthesis of imidazole-4-acetic acid
Weirui Zhao
Huanru Ding
Sheng Hu
Jun Huang
Changjiang Lv
Jiaqi Mei
Zhihua Jin
Shanjing Yao
Lehe Mei
Biotechnology Letters, 2018, 40 : 1049 - 1055
[46] Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A
Bergman, J
Koch, E
Pelcman, B
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16): : 2609 - 2614
[47] EFFECT OF INDOLE-ACETIC ACID ON SYNTHESIS OF RNA AND PROTEINS IN ESCHERICHIA-COLI
DROBISHEVA, NA
DROBISHEV, VI
IZVESTIYA AKADEMII NAUK SSSR SERIYA BIOLOGICHESKAYA, 1978, (01): : 65 - 70
[48] METABOLISM AND SYNTHESIS OF INDOLE-3-ACETIC-ACID (IAA) IN ZEA-MAYS
JENSEN, PJ
BANDURSKI, RS
PLANT PHYSIOLOGY, 1994, 106 (01) : 343 - 351
[49] Synthesis of [13C]-isotopomers of indole and tryptophan for use in the analysis if indole-3-acetic acid biosynthesis
Ilic, N
Cohen, JD
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2004, 47 (10): : 635 - 646
[50] Microbiota-Derived Tryptophan Metabolite Indole-3-Acetic Acid Improves Chemoresistance in Pancreatic Ductal Adenocarcinoma
Wei, Wenjie
Wu, Baibei
Zhang, Wenxin
Zhang, Niya
Luo, Xinli
Cao, Zhaohui
Hu, Xiaobo
PANCREAS, 2023, 52 (05) : E305 - E306

← 1 2 3 4 5 →