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Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin |
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| Authors: | Hidefumi Makabe Masaharu Higuchi Masatoshi Murai |
| Affiliation: | a Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, 8304 Minami-minowa, Kamiina, Nagano 399-4598, Japan b Department of Chemistry, Graduate School of Medical Sciences, Kyoto Prefectural University of Medicine, Kita-ku, Kyoto 603-8334 Japan c Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kita-shirakawa, Sakyo-ku, Kyoto 606-8502, Japan |
| Abstract: | A convergent synthesis of (4R,15R,16R,21S)-rollicosin (1) and (4R,15S,16S,21S)-rollicosin (2) was accomplished. Hydroxy lactone 6a and/or 6b were synthesized from 4-pentyn-1-ol, and α,β-unsaturated lactone 7 was synthesized from γ-lactone 8 and 5-hexen-1-ol. Inhibitory activity of these compounds was examined with bovine heart mitochondrial complex I. |
| Keywords: | Annonaceous acetogenin Antitumor Mitochondrial complex I |
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