Synthesis of (+)-altholactone, (+)-7-epi-altholactone, (-)-etharvensin, and (+)-alumheptolide-A using Pd-catalyzed carbonylation

被引:6
作者
Miyazawa, Yuki [1 ]
Hattori, Yasunao [2 ]
Makabe, Hidefumi [1 ]
机构
[1] Shinshu Univ, Grad Sch Sci & Technol, Dept Agr, Div Food Sci & Biotechnol, 8304 Minami Minowa, Nagano 3994598, Japan
[2] Kyoto Pharmaceut Univ, Ctr Instrumental Anal, Yamashina Ku, Kyoto 6078412, Japan
关键词
Natural product; Polyketides; Styryl lactone; Carbonylation; ENANTIOSELECTIVE SYNTHESES; STYRYL-LACTONE; D-GLUCOSE; (+)-GONIOFUFURONE; (+)-GONIOPYPYRONE; ISOALTHOLACTONE; STYRYLLACTONES; (+)-GONIOTRIOL; SEMISYNTHESIS; CYTOTOXICITY;
D O I
10.1016/j.tetlet.2018.09.062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of (+)-altholactone isolated from Goniothalamus giganteus and its C-7 epimer (+)-7-epi-altholactone, (-)-etharvensin and (+)-alumheptolide-A were achieved. The lactone ring of these compounds was constructed using Pd-catalyzed carbonylation. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4024 / 4027
页数:4
相关论文
共 29 条
[1]   The first total synthesis of (+)-goniothalesacetate and syntheses of (+)-altholactone, (+)-gonioheptolide A, and (-)-goniofupyrone by an asymmetric acetate aldol approach [J].
AnkiReddy, Sandeep ;
AnkiReddy, Praveen ;
Sabitha, Gowravaram .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (42) :10487-10495
[2]   Preparation of 7-alkoxylated furanopyrones:: Semisynthesis of (-)-etharvensin, a new styryl-Lactone from Goniothalamus arvensis [J].
Bermejo, A ;
Blazquez, MA ;
Serrano, A ;
Zafra-Polo, MC ;
Cortes, D .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (12) :1338-1340
[3]   Enantiospecific semisynthesis of (+)-almuheptolide-A, a novel natural heptolide inhibitor of the mammalian mitochondrial respiratory chain [J].
Bermejo, A ;
Tormo, JR ;
Cabedo, N ;
Estornell, E ;
Figadere, B ;
Cortes, D .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (26) :5158-5166
[4]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[5]  
EI-Zayat A. A. E., 1985, TETRAHEDRON LETT, V26, P955
[6]  
EI-Zayat A. A. E., 1989, TETRAHEDRON, V45, P2627
[7]   Asymmetric synthesis of (+)-altholactone: A styryllactone isolated from various goniothalamus species [J].
Enders, Dieter ;
Barbion, Julien .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (09) :2842-2849
[8]   Vinylsilane-mediated synthesis of styryl-lactone frameworks [J].
Fearnley, Stephen Philip ;
Lory, Pedro .
TETRAHEDRON, 2016, 72 (09) :1161-1167
[9]   ENANTIODIVERGENT SYNTHESIS OF (+) AND (-) ALTHOLACTONE FROM D-GLUCOSE - PREPARATION AND CYTO-TOXIC ACTIVITY OF ANALOGS [J].
GESSON, JP ;
JACQUESY, JC ;
MONDON, M .
TETRAHEDRON, 1989, 45 (09) :2627-2640
[10]  
GESSON JP, 1987, TETRAHEDRON LETT, V28, P3945, DOI 10.1016/S0040-4039(00)96427-X