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Total syntheses and stereochemical reassignments of mollenines A and B.
Shiomi, Shinya; Wada, Kohei; Umeda, Yuhei; Kato, Hikaru; Tsukamoto, Sachiko; Ishikawa, Hayato.
Afiliação
  • Shiomi S; Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto 860-8555, Japan.
  • Wada K; Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto 860-8555, Japan.
  • Umeda Y; Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto 860-8555, Japan.
  • Kato H; Department of Natural Medicines, Graduate School of Pharmaceutical Sciences, Kumamoto University, Oe-honmachi 5-1, Chuo-ku, Kumamoto 862-0973, Japan.
  • Tsukamoto S; Department of Natural Medicines, Graduate School of Pharmaceutical Sciences, Kumamoto University, Oe-honmachi 5-1, Chuo-ku, Kumamoto 862-0973, Japan.
  • Ishikawa H; Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto 860-8555, Japan. Electronic address: h_ishikawa@kumamoto-u.ac.jp.
Bioorg Med Chem Lett ; 28(16): 2766-2769, 2018 09 01.
Article em En | MEDLINE | ID: mdl-29439900
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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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Morfolinas Idioma: En Ano de publicação: 2018 Tipo de documento: Article
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Morfolinas Idioma: En Ano de publicação: 2018 Tipo de documento: Article