443305-05-3Relevant academic research and scientific papers
Chemistry and biology of khafrefungin. Large-scale synthesis, design, and structure-activity relationship of khafrefungin, an antifungal agent
Nakamura, Masayuki,Mori, Yuichiro,Okuyama, Kennichi,Tanikawa, Kunihiro,Yasuda, Satoshi,Kanada, Kentaro,Kobayashi, Shu
, p. 3362 - 3376 (2007/10/03)
Large-scale synthesis, design, and structure-activity relationships of khafrefungin are reported. Khafrefungin is an antifungal agent that inhibits inositol phosphorylceramide (IPC) synthase, a enzyme involved in fungal sphingolipid biosynthesis. Unlike o
Efficient total synthesis of khafrefungin: Convergent approach using Suzuki coupling under thallium-free conditions toward multigram-scale synthesis
Mori, Yuichiro,Nakamura, Masayuki,Wakabayashi, Takeshi,Mori, Kouhei,Kobayashi, Shu
, p. 601 - 603 (2007/10/03)
An efficient and practical synthetic route to khafrefungin, an antifungal agent, has been developed based on successive coupling of three components, 3, 4, and then 2. A key step of the synthesis is the Suzuki coupling of 2 and 10, in which the use of tox
Total synthesis and structural elucidation of khafrefungin
Wakabayashi,Mori,Kobayashi
, p. 1372 - 1375 (2007/10/03)
Total synthesis and structural elucidation of khafrefungin, a novel antifungal agent isolated from the fermentation culture MF6020, have been achieved. Unlike other inhibitors that inhibit the corresponding enzyme in fungi and mammals to the same extent,
Convergent total synthesis of khafrefungin and its inhibitory activity of fungal sphingolipid syntheses
Kobayashi,Mori,Wakabayashi,Yasuda,Hanada
, p. 5580 - 5584 (2007/10/03)
A convergent total synthesis of khafrefungin, a novel inhibitor of fungal sphingolipid syntheses isolated from the fermentation culture MF6020, has been developed. Alkenylboronic acid 5 and alkenyliodide 6, key fragments for the total synthesis, were prepared from the corresponding achiral aldehydes using tin(II)-catalyzed and Zr(IV)-catalyzed asymmetric aldol reactions, respectively. The Suzuki coupling reaction of these two fragments was successfully performed to give 17 in good yield. Through the total synthesis, epimerization of the C4 position having a rather highly acidic proton did not occur, indicating that khafrefungin was under strict conformational constraints to prevent the epimerization process. This characteristic stability of khafrefungin has also been discussed using semiempirical calculation and synthesis. Finally, khafrefungin derivatives have also been synthesized, and their antifungal activities have been measured to obtain information on the structure-activity relationships.
