Efficient two directional syntheses of a homophthalate ester and novel resorcylate oligomers

被引:15
作者
Patel, Bhavesh H. [1 ]
Heath, Scott F. A. [1 ]
Mason, Andrew M. [2 ]
Barrett, Anthony G. M. [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] GlaxoSmithKline R&D, Stevenage SG1 2NY, Herts, England
基金
英国工程与自然科学研究理事会;
关键词
Resorcylate; Double dioxinone; Homophthalate ester; Aromatization; BIOMIMETIC SYNTHESIS; NATURAL-PRODUCTS; AROMATIZATION;
D O I
10.1016/j.tetlet.2011.01.100
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thermolysis of 6,6'-(2-oxopropane-1,3-diyl)bis(2,2-dimethyl-4H-1,3-dioxin-4-one) in the presence of methanol gave a triketo-ester which subsequently aromatized to provide a synthetically useful homophthalate ester. Enolate C-acylation in the presence of diethylzinc was used to synthesize other double diketo-dioxinones, which on cyclization, aromatization and dioxinone ring opening gave novel double resorcylate derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2258 / 2261
页数:4
相关论文
共 17 条
[1]   CONVENIENT SYNTHESES OF ALKYL BETA-RESORCYLATE DERIVATIVES [J].
BARRETT, AGM ;
MORRIS, TM ;
BARTON, DHR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10) :2272-2277
[2]   Studies on the resorcylates: biomimetic total syntheses of (+)-montagnetol and (+)-erythrin [J].
Basset, Jean-Francois ;
Leslie, Colin ;
Hamprecht, Dieter ;
White, Andrew J. P. ;
Barrett, Anthony G. M. .
TETRAHEDRON LETTERS, 2010, 51 (05) :783-785
[3]  
BUCHI G, 1986, J ORG CHEM, V51, P4813
[4]   Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation-Trapping-Aromatization Sequence [J].
Calo, Frederick ;
Richardson, Jeffery ;
Barrett, Anthony G. M. .
ORGANIC LETTERS, 2009, 11 (21) :4910-4913
[5]   SYNTHESIS OF POLYKETIDE-TYPE AROMATIC NATURAL-PRODUCTS BY BIOGENETICALLY MODELED ROUTES [J].
HARRIS, TM ;
HARRIS, CM .
TETRAHEDRON, 1977, 33 (17) :2159-2185
[6]   THERMAL-DECOMPOSITION OF "2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE AND 1-ETHOXYBUTYN-3-ONE - ACETYLKETENE [J].
HYATT, JA ;
FELDMAN, PL ;
CLEMENS, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5105-5108
[7]   New DNA binding ligands as a model of chromomycin A3 [J].
Imoto, S ;
Haruta, Y ;
Watanabe, K ;
Sasaki, S .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (19) :4855-4859
[8]   Synthesis of 4-acetylisocoumarin: First total syntheses of AGI-7 and sescandelin [J].
Kim, S ;
Fan, GJ ;
Lee, J ;
Lee, JJ ;
Kim, D .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3127-3130
[9]   A novel biomimetic synthesis of (S)-(-)-zearalenone: via macrocyclization and transannular aromatization [J].
Miyatake-Ondozabal, Hideki ;
Barrett, Anthony G. M. .
TETRAHEDRON, 2010, 66 (33) :6331-6334
[10]   AN ORGANOZINC AID IN ALKYLATION AND ACYLATION OF LITHIUM ENOLATES [J].
MORITA, Y ;
SUZUKI, M ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1785-1787