SYNTHESIS OF (+/-)-HALIPANICINE, A MARINE SESQUITERPENE ISOTHIOCYANATE ISOLATED FROM AN OKINAWAN MARINE SPONGE HALICHONDRIA-PANICEA

被引:12
|
作者
NAKAMURA, H
YE, B
MURAI, A
机构
[1] Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo
关键词
HALIPANICINE; MARINE SESQUITERPENE ISOTHIOCYANATE; MARINE SPONGE; HALICHONDRIA-PANICEA;
D O I
10.1016/S0040-4039(00)74733-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-)-Halipanicine, 4-isothiocyanato-1-cadinene, isolated from an Okinawan marine sponge Halichondria panacea was synthesized from (+/-)-cryptone in 21 steps in 7.7% total yield. The regio- and stereospecific synthesis esablished the relative stereochemistry of halipanicine.
引用
收藏
页码:8113 / 8116
页数:4
相关论文
共 50 条
  • [31] Solid phase total synthesis of callipeltin E isolated from marine sponge Latrunculia sp.
    Kikuchi, Mari
    Nosaka, Kazuto
    Akaji, Kenichi
    Konno, Hiroyuki
    TETRAHEDRON LETTERS, 2011, 52 (30) : 3872 - 3875
  • [32] Marine natural products .36. Biologically active polyacetylenes, adociacetylenes A, B, C, and D, from an Okinawan marine sponge of Adocia sp.
    Kobayashi, M
    Mahmud, T
    Tajima, H
    Wang, WQ
    Aoki, S
    Nakagawa, S
    Mayumi, T
    Kitagawa, I
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (04) : 720 - 724
  • [33] New Trisulfated Steroids from the Vietnamese Marine Sponge Halichondria vansoesti and Their PSA Expression and Glucose Uptake Inhibitory Activities
    Tabakmakher, Kseniya M.
    Makarieva, Tatyana N.
    Denisenko, Vladimir A.
    Popov, Roman S.
    Dmitrenok, Pavel S.
    Dyshlovoy, Sergey A.
    Grebnev, Boris B.
    Bokemeyer, Carsten
    von Amsberg, Gunhild
    Cuong, Nguyen X.
    MARINE DRUGS, 2019, 17 (08)
  • [34] MARINE NATURAL-PRODUCTS .24. THE ABSOLUTE STEREOSTRUCTURE OF MISAKINOLIDE-A, A POTENT CYTOTOXIC DIMERIC MACROLIDE FROM AN OKINAWAN MARINE SPONGE THEONELLA SP
    TANAKA, J
    HIGA, T
    KOBAYASHI, M
    KITAGAWA, I
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) : 2967 - 2970
  • [35] Diversity of culturable actinobacteria isolated from marine sponge Haliclona sp.
    Jiang, Shumei
    Sun, Wei
    Chen, Minjie
    Dai, Shikun
    Zhang, Long
    Liu, Yonghong
    Lee, Kyung Jin
    Li, Xiang
    ANTONIE VAN LEEUWENHOEK INTERNATIONAL JOURNAL OF GENERAL AND MOLECULAR MICROBIOLOGY, 2007, 92 (04): : 405 - 416
  • [36] Secomycalolide A:: A new proteasome inhibitor isolated from a marine sponge of the genus Mycale
    Tsukamoto, Sachiko
    Koimaru, Keiichirou
    Ohta, Tomihisa
    MARINE DRUGS, 2005, 3 (02): : 29 - 35
  • [37] Diversity of culturable actinobacteria isolated from marine sponge Haliclona sp.
    Shumei Jiang
    Wei Sun
    Minjie Chen
    Shikun Dai
    Long Zhang
    Yonghong Liu
    Kyung Jin Lee
    Xiang Li
    Antonie van Leeuwenhoek, 2007, 92 : 405 - 416
  • [38] Erythrobacter spongiae sp. nov., isolated from marine sponge
    Zhuang, Lingping
    Lin, Binbin
    Xu, Li
    Li, Guoqiang
    Wu, Chang-Jer
    Luo, Lianzhong
    INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY, 2019, 69 (04) : 1111 - 1116
  • [39] A NEW 5-ALPHA,8-ALPHA-EPIDIOXY STEROL FROM THE OKINAWAN MARINE SPONGE OF THE AXINYSSA GENUS
    IGUCHI, K
    SHIMURA, H
    YANG, Z
    YAMADA, Y
    STEROIDS, 1993, 58 (09) : 410 - 413
  • [40] Roseovarius spongiae sp. nov., a bacterium isolated from marine sponge
    Zhuang, Lingping
    Luo, Lianzhong
    INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY, 2020, 70 (01) : 274 - 281