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
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 45期
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
    AnkiReddy, Sandeep
    AnkiReddy, Praveen
    Sabitha, Gowravaram
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (42) : 10487 - 10495
  • [2] Preparation of 7-alkoxylated furanopyrones:: Semisynthesis of (-)-etharvensin, a new styryl-Lactone from Goniothalamus arvensis
    Bermejo, A
    Blazquez, MA
    Serrano, A
    Zafra-Polo, MC
    Cortes, D
    [J]. 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
    Bermejo, A
    Tormo, JR
    Cabedo, N
    Estornell, E
    Figadere, B
    Cortes, D
    [J]. 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
    Enders, Dieter
    Barbion, Julien
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (09) : 2842 - 2849
  • [8] Vinylsilane-mediated synthesis of styryl-lactone frameworks
    Fearnley, Stephen Philip
    Lory, Pedro
    [J]. TETRAHEDRON, 2016, 72 (09) : 1161 - 1167
  • [9] ENANTIODIVERGENT SYNTHESIS OF (+) AND (-) ALTHOLACTONE FROM D-GLUCOSE - PREPARATION AND CYTO-TOXIC ACTIVITY OF ANALOGS
    GESSON, JP
    JACQUESY, JC
    MONDON, M
    [J]. TETRAHEDRON, 1989, 45 (09) : 2627 - 2640
  • [10] GESSON JP, 1987, TETRAHEDRON LETT, V28, P3945, DOI 10.1016/S0040-4039(00)96427-X
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