Synthesis of a Series of Hydroxycarboxylic Acids as Standards for Oxidation of Nonanoic Acid

被引:13
作者
Rajabi, Mehdi [1 ]
Lanfranchi, Moreno [1 ]
Campo, Federica [1 ]
Panza, Luigi [1 ]
机构
[1] Univ Piemonte Orientale, Dipartimento Sci Farmaco, I-28100 Novara, Italy
关键词
macrolactone; IBX; natural products; hydroxycarboxylic acid; Grignard; BAEYER-VILLIGER OXIDATION; HYDROGEN-PEROXIDE; FATTY-ACIDS; CYTOCHROME-P450; KETONES;
D O I
10.1080/00397911.2013.853800
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a series of nonanoic acids hydroxylated in terminal,omega-1,omega-2,omega-3 positions is described. These compounds will be employed as useful standards for the study of enzymatic and microbiological oxidation of nonanoic acid. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
引用
收藏
页码:1149 / 1154
页数:6
相关论文
共 35 条
[1]   SYNTHESIS AND BIOLOGICAL PROPERTIES OF SOME NOVEL HETEROCYCLIC HOMOPROSTANOIDS [J].
BENDER, AD ;
BERKOFF, CE ;
GROVES, WG ;
SOFRANKO, LM ;
WELLMAN, GR ;
LIU, JH ;
BEGOSH, PP ;
HORODNIAK, JW .
JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (11) :1094-1098
[2]  
Dal Farra C., 2002, Patent, Patent No. [WO2002072053, 2002072053]
[3]  
DAL FC, 2002, CHEM ABSTR, V137
[4]   CONVENIENT PREPARATION OF 10-HYDROXYDECANOIC ACID [J].
ELLIGER, CA ;
DIAMOND, MJ .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1972, 49 (04) :278-&
[5]  
FISCHER R, 1999, CHEM ABSTR, V130
[6]  
FOQUE E, 1989, SYNTHESIS-STUTTGART, P661
[7]   PREPARATION OF LAURYL ALCOHOL AND 6-HYDROXYCAPROIC ACID FROM PETROSELINIC ACID [J].
FORE, SP ;
WARD, TL ;
DOLLEAR, FG .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1963, 40 (01) :30-&
[8]   ABOUT THE STEREOSPECIFIC ALPHA-ALKYLATION OF BETA-HYDROXYESTERS [J].
FRATER, G .
HELVETICA CHIMICA ACTA, 1979, 62 (08) :2825-2828
[9]   A user-friendly entry to 2-iodoxybenzoic acid (IBX) [J].
Frigerio, M ;
Santagostino, M ;
Sputore, S .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4537-4538
[10]   Clinical and cosmeceutical uses of hydroxyacids [J].
Green, Barbara A. ;
Yu, Ruey J. ;
Van Scott, Eugene J. .
CLINICS IN DERMATOLOGY, 2009, 27 (05) :495-501