Total syntheses and stereochemical reassignments of mollenines A and B |
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| Authors: | Shinya Shiomi Kohei Wada Yuhei Umeda Hikaru Kato Sachiko Tsukamoto Hayato Ishikawa |
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| Affiliation: | 1. Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto 860-8555, Japan;2. Department of Natural Medicines, Graduate School of Pharmaceutical Sciences, Kumamoto University, Oe-honmachi 5-1, Chuo-ku, Kumamoto 862-0973, Japan |
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| Abstract: | Total syntheses of prenylated pyrrolidinoindoline alkaloids, (?)-mollenines A [(?)-1′] and B (2′), were accomplished via three- and four-step sequences including a bioinspired indole prenylation reaction followed by dioxomorpholine ring formation. Then, the stereochemistry of mollenines A and B was reassigned to 3S,6S,14S,16S by analysis of spectroscopic data and chemical syntheses with different approaches along with the comparison of calculated and experimental ECD spectra. In addition, a thermodynamically controlled epimerization reaction on the dioxomorpholine ring was observed in our synthesis. |
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| Keywords: | Mollenine A Mollenine B Bioinspired reaction Total synthesis Dioxomorpholine |
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