An efficient asymmetric synthesis of furofuran lignans: (+)-sesamin and (-)-sesamin

被引:24
|
作者
Kim, JC
Kim, KH
Jung, JC
Park, OS [1 ]
机构
[1] Chungbuk Natl Univ, Coll Nat Sci, Inst Basic Sci, Dept Chem, Chungbuk 361763, South Korea
[2] Univ Mississippi, Dept Med Chem, Sch Pharm, University, MS 38677 USA
关键词
D O I
10.1016/j.tetasy.2005.11.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient synthesis of (+)-sesamin 1a and (-)-sesamin 1b is described. The key reactions include highly stereoselective aldol condensation of piperonal 7 with the dianion of chiral oxazolidinone 8, followed by intramolecular ring cyclization of aldol product 11 in high yield. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:3 / 6
页数:4
相关论文
共 50 条
  • [41] Antioxidant lignans sesamin and sesamolin in sesame (Sesamum indicum L.): A comprehensive review and future prospects
    Dossou, Senouwa Segla Koffi
    Xu Fang-tao
    Dossa, Komivi
    Zhou Rong
    Zhao Ying-zhong
    Wang Lin-hai
    JOURNAL OF INTEGRATIVE AGRICULTURE, 2023, 22 (01) : 14 - 30
  • [42] SESAMIN, SESAMOLIN AND THE ORIGIN OF SESAME
    BEDIGIAN, D
    SEIGLER, DS
    HARLAN, JR
    BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1985, 13 (02) : 133 - 139
  • [43] The mechanism of the antihypertensive effect of sesamin
    Nakano, D
    Ishii, F
    Kawanishi, H
    Ikemura, K
    Kaku, T
    Takaoka, M
    Nakai, M
    Ono, Y
    Kiso, Y
    Tanaka, T
    Matsumura, Y
    JOURNAL OF PHARMACOLOGICAL SCIENCES, 2005, 97 : 119P - 119P
  • [44] Inhibition of two stages of melanin synthesis by sesamol, sesamin and sesamolin
    Srisayam, Montra
    Weerapreeyakul, Natthida
    Kanokmedhakul, Kwanjai
    ASIAN PACIFIC JOURNAL OF TROPICAL BIOMEDICINE, 2017, 7 (10) : 886 - 895
  • [45] Sesamin is one of the major precursors of mammalian lignans in sesame seed (Sesamum indicum) as observed in vitro and in rats
    Liu, Z
    Saarinen, NM
    Thompson, LU
    JOURNAL OF NUTRITION, 2006, 136 (04): : 906 - 912
  • [46] Antioxidant lignans sesamin and sesamolin in sesame(Sesamum indicum L.): A comprehensive review and future prospects
    Senouwa Segla Koffi DOSSOU
    XU Fang-tao
    Komivi DOSSA
    ZHOU Rong
    ZHAO Ying-zhong
    WANG Lin-hai
    Journal of Integrative Agriculture, 2023, 22 (01) : 14 - 30
  • [47] Inhibition of two stages of melanin synthesis by sesamol,sesamin and sesamolin
    Montra Srisayam
    Natthida Weerapreeyakul
    Kwanjai Kanokmedhakul
    Asian Pacific Journal of Tropical Biomedicine, 2017, 7 (10) : 886 - 895
  • [48] Inhibitory effects of sesamin on human osteoclastogenesis
    Wanachewin, Orawan
    Pothacharoen, Peraphan
    Kongtawelert, Prachya
    Phitak, Thanyaluck
    ARCHIVES OF PHARMACAL RESEARCH, 2017, 40 (10) : 1186 - 1196
  • [49] PROTON MAGNETIC RESONANCE IN SESAMIN AND ASARININS
    GOVIL, G
    KHETRAPAL, CL
    KANEKAR, CR
    CURRENT SCIENCE, 1961, 30 (07): : 252 - &
  • [50] Decomposition reaction of sesamin in supercritical water
    Nakai, Masaaki
    Kageyama, Norihiko
    Nakahara, Koichi
    Miki, Wataru
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2006, 70 (05) : 1273 - 1276