Preparation of 7-alkoxylated furanopyrones:: Semisynthesis of (-)-etharvensin, a new styryl-Lactone from Goniothalamus arvensis

被引:17
作者
Bermejo, A [1 ]
Blazquez, MA [1 ]
Serrano, A [1 ]
Zafra-Polo, MC [1 ]
Cortes, D [1 ]
机构
[1] Univ Valencia, Fac Farm, Dept Farmacol Farmacognosia & Farmacodinam, Burjassot 46100, Valencia, Spain
来源
JOURNAL OF NATURAL PRODUCTS | 1997年 / 60卷 / 12期
关键词
D O I
10.1021/np970346w
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A new furanopyrone derivative, (-)-etharvensin (1), was isolated from the stem bark of Goniothalamus arvensis. Semisynthesis of the 7-ethoxyfuranopyrone 1 was achieved by addition of EtOH in concentrated acid medium to the unsaturated alpha-pyrone (+)-altholactone (2). This protocol constitutes a novel, direct (single-step), and efficient method to prepare this class of bioactive compounds.
引用
收藏
页码:1338 / 1340
页数:3
相关论文
共 10 条
[1]   (+)-GONIOTHARVENSIN, A NOVEL STYRYL-LACTONE FROM THE STEM BARK OF GONIOTHALAMUS-ARVENSIS [J].
BERMEJO, A ;
LORA, MJ ;
BLAZQUEZ, MA ;
RAO, KS ;
CORTES, D ;
ZAFRAPOLO, MC .
NATURAL PRODUCT LETTERS, 1995, 7 (02) :117-122
[2]  
BERMEJO A, 1997, IN PRESS PHYTOCHEMIS
[3]  
Cave A, 1997, Fortschr Chem Org Naturst, V70, P81
[4]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[5]  
ELZAYAT AE, 1985, TETRAHEDRON LETT, V29, P955
[6]  
MCLAUGHLIN JL, 1993, ACS SYM SER, V534, P112
[7]   First total synthesis and structural elucidation of (-)-goniofupyrone [J].
Mukai, C ;
Hirai, S ;
Kim, IJ ;
Hanaoka, M .
TETRAHEDRON LETTERS, 1996, 37 (30) :5389-5392
[8]   Functional evidence of inverse agonism in vascular smooth muscle [J].
Noguera, MA ;
Ivorra, MD ;
DOcon, P .
BRITISH JOURNAL OF PHARMACOLOGY, 1996, 119 (01) :158-164
[9]   DETERMINATION OF ABSOLUTE-CONFIGURATION OF STEREOGENIC CARBINOL CENTERS IN ANNONACEOUS ACETOGENINS BY H-1-NMR AND F-19-NMR ANALYSIS OF MOSHER ESTER DERIVATIVES [J].
RIESER, MJ ;
HUI, YH ;
RUPPRECHT, JK ;
KOZLOWSKI, JF ;
WOOD, KV ;
MCLAUGHLIN, JL ;
HANSON, PR ;
ZHUANG, ZP ;
HOYE, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10203-10213
[10]   Acetogenins from annonaceae, inhibitors of mitochondrial complex I [J].
ZafraPolo, MC ;
Gonzalez, MC ;
Estornell, E ;
Sahpaz, S ;
Cortes, D .
PHYTOCHEMISTRY, 1996, 42 (02) :253-271