Synthesis of the KLMN Fragment of Gymnocin-A from the FGH Fragment

被引:4
|
作者
Sakai, Takeo [1 ]
Ishihara, Aoi [1 ]
Mori, Yuji [1 ]
机构
[1] Meijo Univ, Fac Pharm, Tempaku Ku, 150 Yagotoyama, Nagoya, Aichi 4688503, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 07期
基金
日本学术振兴会;
关键词
TRANS-FUSED TETRAHYDROPYRANS; OXIRANYL ANION STRATEGY; RED TIDE DINOFLAGELLATE; POLYCYCLIC ETHERS; RING FRAGMENT; CONVERGENT STRATEGIES; CYTOTOXIC POLYETHER; MARINE POLYETHER; TOXINS; ACID;
D O I
10.1021/acs.joc.7b00232
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An improved route for the synthesis of the KLMN fragment of gymnocin-A was developed through the oxiranyl anion coupling of the FGH fragment with a chiral C-3 epoxy sulfone, followed by 6-endo cyclization. This straightforward approach reduced the number of synthetic steps by 14 compared with a previous route, using alternative building blocks.
引用
收藏
页码:3976 / 3981
页数:6
相关论文
共 50 条
  • [31] STEREOCONTROLLED SYNTHESIS OF A POLYETHER FRAGMENT
    BARTLETT, PA
    HOLM, KH
    MORIMOTO, A
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25): : 5179 - 5183
  • [32] SYNTHESIS OF THE UPPER FRAGMENT OF TETRONOLIDE
    TAKEDA, K
    KATO, H
    SASAHARA, H
    YOSHII, E
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (15) : 1197 - 1198
  • [33] Synthesis of the FG fragment of the pectenotoxins
    Heapy, Amanda M.
    Wagner, Thomas W.
    Brimble, Margaret M.
    SYNLETT, 2007, (15) : 2359 - 2362
  • [34] Synthesis of the ABC fragment of the pectenotoxins
    Halim, R
    Brimble, MA
    Merten, J
    ORGANIC LETTERS, 2005, 7 (13) : 2659 - 2662
  • [35] The synthesis of fragment A of an antibiotic, nosiheptide
    Umemura, K
    Noda, H
    Yoshimura, J
    Konn, A
    Yonezawa, Y
    Shin, CG
    TETRAHEDRON LETTERS, 1997, 38 (20) : 3539 - 3542
  • [36] A 'Fragment from Mexico'
    Tomlinson, C
    HUDSON REVIEW, 2002, 54 (04): : 572 - 572
  • [37] FROM BOOK TO FRAGMENT
    Mari, Antoni
    FORMA-REVISTA D ESTUDIS COMPARATIUS ART LITERATURA PENSAMENT, 2009, : 13 - 18
  • [38] 'Fragment from Rome'
    Brenneman, M
    POETRY, 2000, 176 (06) : 325 - 325
  • [39] From Sketch to Fragment
    Schaeffer, Jean-Marie
    UNIVERSITAS-MONTHLY REVIEW OF PHILOSOPHY AND CULTURE, 2020, 47 (03): : 5 - 18
  • [40] A 'Fragment From a Play'
    Somlyo, G
    HUNGARIAN QUARTERLY, 1998, 39 (151): : 52 - 54