Development of Practical Synthetic Method toward Mechanistic Elucidation of Biologically Active Natural Products

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  • 生物活性天然有機化合物の機能解明を指向した実践的合成手法の開発
  • セイブツ カッセイ テンネン ユウキ カゴウブツ ノ キノウ カイメイ オ シコウ シタ ジッセンテキ ゴウセイ シュホウ ノ カイハツ

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Abstract

The limited supplies of biologically active natural products from natural source have been a severe bottleneck for their application to medical care or mechanistic study of their functions. Synthetic organic chemistry may become a best possible solution of this supply problem by the development of practical synthetic methods suited to the intended molecules. For right-half of halichondrin B, we established a new catalytic cycle of Cr-mediated coupling reaction, new asymmetric Ni/Cr-mediated coupling reaction, surprisingly efficient catalytic Cr-mediated coupling reaction, catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques, and effective device for forming polycyclic ring system of halichondrin B. For mugineic acid, we established the practical synthesis of 2'-deoxy mugineic acid with minimal requirements for workup and purification procedure, efficient synthesis of mugineic acid, and synthesis of mugineic acid derivatives as molecular probes. For E-ring of palau'amine, we established Hg(OTf)2-catalyzed olefin cyclization reactions, and its application to the construction of tetra-substituted carbon center possessing nitrogen that corresponds to C16 position of palau'amine.

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