314270-80-9Relevant academic research and scientific papers
Synthesis and antitumor activities of aquayamycin and analogues of derhodinosylurdamycin A
Acharya, Padam P.,Khatri, Hem Raj,Janda, Sandip,Zhu, Jianglong
supporting information, p. 2691 - 2704 (2019/03/12)
Total syntheses of aquayamycin (3) and a number of analogues of angucycline antitumor antibiotic derhodinosylurdamycin A bearing various 2-deoxy sugar subunits (4-7) have been achieved. These molecules (3-7) were synthesized based on a convergent strategy for the synthesis of derhodinosylurdamycin A (2) previously reported from our group. In particular, our recently developed mild cationic gold-catalyzed glycosylation with S-but-3-ynyl thioglycoside donors was employed for the synthesis of analogues (6 and 7) bearing disaccharide subunits containing α-l-olivoside and α-l-olioside moiety, respectively. Aquayamycin (3), analogues (4-7), and our previously synthesized derhodinosylurdamycin A (2) were then submitted to the Development Therapeutics Program of the National Cancer Institute of National Institutes of Health for the NCI-60 Human Tumor Cell Lines Screening using standard protocols. It was found that derhodinosylurdamycin A (2), aquayamycin (3), and three other analogues (5-7) bearing sugar subunits did not show significant antiproliferative activity against those cancer cell lines. Interestingly, analogue (4) bearing no sugar subunit demonstrates good potential for growth inhibition and cytotoxic activity against a variety of human cancer cell lines.
Total Synthesis of Aquayamycin
Kusumi, Shunichi,Nakayama, Harunobu,Kobayashi, Takumi,Kuriki, Hajime,Matsumoto, Yuka,Takahashi, Daisuke,Toshima, Kazunobu
, p. 18733 - 18736 (2016/12/26)
An efficient and practical total synthesis of aquayamycin has been accomplished. The highly oxidized and stereochemically complex tetracyclic ring system was constructed using three key reactions: 1) highly diastereoselective 1,2-addition of C-glycosyl naphthyllithium to a cyclic ketone, 2) indium-mediated site-selective allylation-rearrangement sequence of naphthoquinone, and 3) diastereoselective intramolecular pinacol coupling. This synthetic strategy offers a novel and efficient pathway to prepare aquayamycin-type angucycline antibiotics.
Synthetic study of aquayamycin. Part 3: First total synthesis
Matsumoto,Yamaguchi,Tanabe,Yasui,Suzuki
, p. 8393 - 8396 (2007/10/03)
The first total synthesis of aquayamycin (1) has been accomplished. The crucial steps include (1) the Hauser reaction between 3-(phenylsulfonyl)phthalide 3 and cyclohexenone 4 to make up the linear BCD tricycle, and (2) the intramolecular pinacol coupling
