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
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