Total Synthesis and Absolute Stereochemistry of Seragakinone A

被引:49
|
作者
Takada, Akiomi [1 ]
Hashimoto, Yoshimitsu [1 ]
Takikawa, Hiroshi [1 ]
Hikita, Katsuyoshi [1 ]
Suzuki, Keisuke [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan
关键词
antibiotics; cyclization; natural products; organocatalysis; total synthesis; AROMATIC NITRILE OXIDES; PROMOTED CYCLOCONDENSATION; ASYMMETRIC EPOXIDATION; HYPERVALENT IODINE; ISOXAZOLES; CONVERSION; CONSTRUCTION; OXIDATION; ALDEHYDES;
D O I
10.1002/anie.201006528
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Cyclic transformation: The key transformations of the asymmetric total synthesis of the marine-derived natural product seragakinone A are two N-heterocyclic carbene catalyzed benzoin cyclizations that result in the construction of two rings and a pinacol-type rearrangement to install the angular prenyl substituent. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2297 / 2301
页数:5
相关论文
共 50 条
  • [41] Total Synthesis, Assignment of the Relative and Absolute Stereochemistry, and Structural Reassignment of Phostriecin (aka Sultriecin)
    Burke, Christopher P.
    Haq, Nadia
    Boger, Dale L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (07) : 2157 - +
  • [42] First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry
    Hayashi, Y
    Shoji, M
    Mukaiyama, T
    Gotoh, H
    Yamaguchi, S
    Nakata, M
    Kakeya, H
    Osada, H
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14): : 5643 - 5654
  • [43] Determination of absolute stereochemistry, total synthesis, and evaluation of peptides from the myxomycete Physarum melleum
    Hanazawa, Shuwa
    Arai, Midori A.
    Li, Xiaofan
    Ishibashi, Masarni
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (01) : 95 - 98
  • [44] Assignment of absolute stereochemistry and total synthesis of (-)-spongidepsin (vol 6, pg 2056, 2004)
    Ghosh, AK
    Xu, XM
    ORGANIC LETTERS, 2004, 6 (14) : 2490 - 2490
  • [45] The naturally occurring ketene acetal benesudon: Total synthesis and assignment of relative and absolute stereochemistry
    Clive, Derrick L. J.
    Minaruzzaman
    Yang, Haikang
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6743 - 6752
  • [46] Total Syntheses of (+)-Echinopine A and B: Determination of Absolute Stereochemistry
    Magauer, Thomas
    Mulzer, Johann
    Tiefenbacher, Konrad
    ORGANIC LETTERS, 2009, 11 (22) : 5306 - 5309
  • [47] Total Syntheses of (+)-GrandilodineC and (+)-LapidilectineB and Determination of their Absolute Stereochemistry
    Nakajima, Masaya
    Arai, Shigeru
    Nishida, Atsushi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (10) : 3473 - 3476
  • [48] TOTAL SYNTHESIS AND STEREOCHEMISTRY OF HYBRIDALACTONE
    COREY, EJ
    DE, B
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (09) : 2735 - 2736
  • [49] DESOXYSCHIZANDRIN, STEREOCHEMISTRY AND TOTAL SYNTHESIS
    GHERA, E
    BENDAVID, Y
    BECKER, D
    TETRAHEDRON LETTERS, 1977, (05) : 463 - 466
  • [50] Total synthesis and stereochemistry of cytoblastin
    Moreno, OA
    Kishi, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) : 8180 - 8181