A concise approach to benzoic acid derivatives bearing an α,β-unsaturated ketone substituent:: Synthesis of methyl taboganate

被引：2

作者：

Detsi, A

Roussis, V

Tsotinis, A

Roussakis, C

Calogeropoulou, T

机构：

[1] Natl Hellen Res Fdn, Inst Organ & Pharmaceut Chem, GR-11635 Athens, Greece

[2] Univ Athens, Fac Pharm, Dept Pharmacognosy & Chem Nat Prod, GR-15771 Athens, Greece

[3] Univ Athens, Fac Pharm, Dept Pharmaceut Chem, GR-15771 Athens, Greece

[4] Fac Pharm, Lab Pharmacol Marine, F-44035 Nantes, France

来源：

SYNLETT | 2005年 / 20期

关键词：

methyl taboganate; alpha; beta-unsaturated ketones; cytotoxicity;

D O I：

10.1055/s-2005-921933

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise route to benzoic acid derivatives bearing an alpha,beta-unsaturated ketone moiety and its application to the synthesis of the natural product methyl taboganate (1) is described. The methodology is based on the addition of a Grignard reagent to an appropriately substituted salicylaldehyde followed by oxidation of the resulting allylic alcohol to the corresponding alpha,beta-unsaturated ketone. The new compounds were tested for their cytotoxic activity.

引用

页码：3131 / 3135

页数：5

共 50 条

[1] Design, synthesis, and anticancer evaluation of novel andrographolide derivatives bearing an α,β-unsaturated ketone moiety
Cai, Wei
Li, Jieyi
Chen, Cheng
Wu, Jiajia
Li, Jiabin
Xue, Xiaowen
BIOORGANIC CHEMISTRY, 2021, 112
[2] CRYSTALLOGRAPHIC DATA FOR METHYL DERIVATIVES OF BENZOIC ACID
ELIAS, JL
GARLIABL.S
ACTA CRYSTALLOGRAPHICA, 1963, 16 (05): : 434 - &
[3] The oxidation of mesityl methyl ketone by potassium permanganate and the preparation of trimethyl benzoic acid
van Scherpenzeel, L
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS ET DE LA BELGIQUE, 1900, 19 : 377 - 385
[4] Synthesis and reactions of the thioamide derivatives of methyl vinyl ketone
Gros, Lukasz
Wesolowska, Aneta
Westerlich, Slawomir
Jagodzinski, Tadeusz
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (01) : 167 - 176
[5] A concise, asymmetric synthesis of tetramic acid derivatives
Fustero, S
de la Torre, MG
Sanz-Cervera, JF
de Arellano, CR
Piera, J
Simón, A
ORGANIC LETTERS, 2002, 4 (21) : 3651 - 3654
[6] Synthesis of Hydroxylated Biphenyl Derivatives Bearing an α,β-Unsaturated Ketone as a Lead Structure for the Development of Drug Candidates against Malignant Melanoma
Dettori, Maria Antonietta
Pisano, Marina
Rozzo, Carla
Delogu, Giovanna
Fabbri, Davide
CHEMMEDCHEM, 2021, 16 (06) : 1022 - 1033
[7] Synthesis and properties of perfluoroalkylalkoxy substituted benzoic acid derivatives
Nishikawa, E
Yamamoto, J
Yokoyama, H
CHEMISTRY LETTERS, 2001, (02) : 94 - 95
[8] QUENCHING ACTION OF BENZOIC ACID AND METHYL BENZOATE ON FLUORESCENCE OF NAPHTHALENE DERIVATIVES
MIWA, T
KOIZUMI, M
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1965, 38 (04) : 529 - +
[9] A Concise Approach for the Total Synthesis of Pseudolaric Acid A
Xu, Tao
Li, Chuang-chuang
Yang, Zhen
ORGANIC LETTERS, 2011, 13 (10) : 2630 - 2633
[10] Asymmetric synthesis of unsaturated pipecolic acid derivatives
Agami, C
Bihan, D
Morgentin, R
PuchotKadouri, C
SYNLETT, 1997, (07) : 799 - +

← 1 2 3 4 5 →