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Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I |
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| Authors: | Hidefumi Makabe Yasunao Hattori Hiroyuki Konno Hideto Miyoshi Takayuki Oritani |
| Institution: | a Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, 8304 Minami-minowa, Kamiina, Nagano 399-4598, Japan b Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-Shimo-Adachi-cho, Sakyo-ku, Kyoto 606-8502, Japan c Division of Applied Sciences, Graduate School of Agriculture, Kyoto University, Kita-shirakawa, Sakyo-ku, Kyoto 606-8502, Japan d College of Technology, Toyama Prefectural University, 5180 Kurokawa, Kosugimachi, Toyama 939-0398, Japan e Department of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University, 1-1, Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai, 981-8555, Japan |
| Abstract: | A convergent total synthesis of cis-solamin (1a) and its diastereomer (1b) was accomplished. A key reaction of this approach was the use of VO(acac)2-catalyzed diastereoselective epoxidation of (Z)-bis-homoallylic alcohol 3 followed by spontaneous cyclization for the cis-THF ring formation. By comparison of the optical rotation of the two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a. Inhibitory action of synthetic 1a and 1b with bovine heart mitochondrial complex I are reported. |
| Keywords: | Annonaceous acetogenin Antitumor Mitochondrial complex I |
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