TOTAL SYNTHESIS OF HYALODENDRIOL C

被引:8
作者
Jeelani, Ishtiaq [1 ]
Itaya, Katsunori [2 ]
Abe, Hitoshi [2 ]
机构
[1] Univ Toyama, Grad Sch Innovat Life Sci, 3190 Gofuku, Toyama 9308555, Japan
[2] Univ Toyama, Fac Engn, 3190 Gofuku, Toyama 9308555, Japan
关键词
BIARYL COUPLING REACTION; DIBENZO-ALPHA-PYRONES; ENDOPHYTIC FUNGUS; FORMAL SYNTHESIS; GRAPHISLACTONE; METABOLITES; DERIVATIVES; BENZOATE; LACTONE; ACID;
D O I
10.3987/COM-21-14480
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We present a total synthesis of hyalodendriol C, a fungal natural product. We have focused on the use of palladium-catalyzed intramolecular biaryl coupling reaction of phenyl benzoate derivatives to synthesize hyalodendriol C. Keeping in view, the indispensable biological values of this compound, we took the advantage of our established strategy to chemically synthesize hyalodendriol C. The total synthesis of hyalodendriol C got accomplished in 10 steps beginning with the preparation of phenol derivative from the commercially available 5-methylbenzene-1,3-diol and synthesis of the corresponding benzoic acid derivative.
引用
收藏
页码:1570 / 1578
页数:9
相关论文
共 31 条
  • [1] Synthesis of graphislactones A-D through a palladium-mediated biaryl coupling reaction of phenyl benzoate derivatives
    Abe, H
    Nishioka, K
    Takeda, S
    Arai, M
    Takeuchi, Y
    Harayama, T
    [J]. TETRAHEDRON LETTERS, 2005, 46 (18) : 3197 - 3200
  • [2] Enantioselective construction of biaryl part in the synthesis of stegane related compounds
    Abe, H
    Takeda, S
    Fujita, T
    Nishioka, K
    Takeuchi, Y
    Harayama, T
    [J]. TETRAHEDRON LETTERS, 2004, 45 (11) : 2327 - 2329
  • [3] SYNTHESIS OF HIGHLY OXYGENATED BIPHENYL DERIVATIVE IN AN OPTICALLY ACTIVE FORM THROUGH PALLADIUM-MEDIATED INTRAMOLECULAR BIARYL COUPLING REACTION
    Abe, Hitoshi
    Arai, Masatsugu
    Nishioka, Keisuke
    Kida, Tatsuya
    Shioe, Kazuma
    Takeuchi, Yasuo
    Harayama, Takashi
    [J]. HETEROCYCLES, 2008, 76 (01) : 291 - 303
  • [4] Enantioselective synthesis of valoneic acid derivative
    Abe, Hitoshi
    Sahara, Yusuke
    Matsuzaki, Yuki
    Takeuchi, Yasuo
    Harayama, Takashi
    [J]. TETRAHEDRON LETTERS, 2008, 49 (04) : 605 - 609
  • [5] Synthesis of alternariol through an intramolecular biaryl coupling reaction using palladium reagent
    Abe, Hitoshi
    Fukumoto, Tomoko
    Takeuchi, Yasuo
    Harayama, Takashi
    [J]. HETEROCYCLES, 2007, 74 : 265 - 271
  • [6] Palladium-mediated intramolecular biaryl coupling reaction for natural product synthesis
    Abe, Hitoshi
    Harayama, Takashi
    [J]. HETEROCYCLES, 2008, 75 (06) : 1305 - 1320
  • [7] SYNTHESIS OF GRAPHISLACTONE H
    Abe, Hitoshi
    Fukumoto, Tomoko
    Horino, Yoshikazu
    Harayama, Takashi
    Takeuchi, Yasuo
    [J]. HETEROCYCLES, 2010, 82 (01) : 851 - 855
  • [8] PREPARATION OF 5H,7H-DIBENZ[c,e]OXEPIN-5-ONE DERIVATIVE THROUGH RECONSTRUCTION OF THE LACTONE RING
    Abe, Hitoshi
    Arai, Masatsugu
    Takeuchi, Yasuo
    Harayama, Takashi
    [J]. HETEROCYCLES, 2009, 77 (02) : 1409 - 1416
  • [9] Ahmed K., 2019, Int. J. Pharm. Biol. Sci, V9, P1000
  • [10] SEQUENTIAL DIRECTED ORTHO METALATION BORONIC ACID CROSS-COUPLING REACTIONS - A GENERAL REGIOSPECIFIC ROUTE TO OXYGENATED DIBENZO[B,D]PYRAN-6-ONES RELATED TO ELLAGIC ACID
    ALO, BI
    KANDIL, A
    PATIL, PA
    SHARP, MJ
    SIDDIQUI, MA
    SNIECKUS, V
    JOSEPHY, PD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) : 3763 - 3768