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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 10期
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
  • [31] TOTAL SYNTHESIS OF THE POLLEN-GROWTH INHIBITOR (-)-EMENIVEOL - ASSIGNMENT OF ABSOLUTE STEREOCHEMISTRY
    SHIMOKAWA, K
    SMITH, AB
    TETRAHEDRON LETTERS, 1993, 34 (46) : 7383 - 7384
  • [32] The first total synthesis and revision of absolute stereochemistry of natural cytotoxic lactone cleistanolate
    Kesic, Jelena
    Kovacevic, Ivana
    Popsavin, Mirjana
    Benedekovic, Goran
    Rodic, Marko V.
    Kojic, Vesna
    Popsavin, Velimir
    BIOORGANIC CHEMISTRY, 2022, 128
  • [33] 1ST ASYMMETRIC TOTAL SYNTHESIS OF (+)-STEGANACIN DETERMINATION OF ABSOLUTE STEREOCHEMISTRY
    TOMIOKA, K
    ISHIGURO, T
    KOGA, K
    TETRAHEDRON LETTERS, 1980, 21 (31) : 2973 - 2976
  • [34] Determination of relative and absolute stereochemistry of cephalosporolide D and its enantioselective total synthesis
    Shiina, I
    Fukuda, Y
    Ishii, T
    Fujisawa, H
    Mukaiyama, T
    CHEMISTRY LETTERS, 1998, (08) : 831 - 832
  • [35] A rapid total synthesis of spirotryprostatin B: Proof of its relative and absolute stereochemistry
    von Nussbaum, F
    Danishefsky, SJ
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (12) : 2175 - +
  • [36] Total synthesis and determination of absolute stereochemistry of apparicines, novel antimalarial indole alkaloids
    Sunazuka, Toshiaki
    Noguchi, Yoshihiko
    Hirose, Tomoyasu
    Furuya, Yujiro
    Tsuchiya, Tatsuhiko
    Ishiyama, Aki
    Otoguro, Kazuhiko
    Omura, Satoshi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [37] Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids
    Shirahata, Tatsuya
    Sunazuka, Toshiaki
    Yoshida, Kiminari
    Yamamoto, Daisuke
    Harigaya, Yoshihiro
    Kuwajima, Isao
    Nagai, Takayuki
    Kiyohara, Hiroaki
    Yamada, Haruki
    Omura, Satoshi
    TETRAHEDRON, 2006, 62 (40) : 9483 - 9496
  • [38] STEREOSELECTIVE SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SINEFUNGIN
    MAGUIRE, MP
    FELDMAN, PL
    RAPOPORT, H
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03): : 948 - 955
  • [39] SYNTHESIS OF NEOCARZILIN-A - AN ABSOLUTE STEREOCHEMISTRY
    NOZOE, S
    KIKUCHI, K
    ISHII, N
    OHTA, T
    TETRAHEDRON LETTERS, 1992, 33 (49) : 7551 - 7552
  • [40] Asymmetric total synthesis of (-)-VM55599: Establishment of the absolute stereochemistry and biogenetic implications
    Sanz-Cervera, JF
    Williams, RM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) : 2556 - 2559
12345