Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation

Satoshi Adachi, Kana Watanabe, Yusuke Iwata, Shunsuke Kameda, Yoshihito Miyaoka, Masao Onozuka, Ryo Mitsui, Yoko Saikawa, Masaya Nakata

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The highly oxygenated polyketide antibiotics, lactonamycin and lactonamycin Z were synthesized. The BCDEF ring system was constructed by a cycloaddition and a palladium-catalyzed cyclization and a Bischler-Napieralski-type cyclization was used for the formation of the A ring. The glycosylation of the aglycon with the appropriate sugar gave lactonamycin and lactonamycin Z.

Original languageEnglish
Pages (from-to)2087-2091
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number7
DOIs
Publication statusPublished - 2013 Feb 11

Keywords

  • Bischler-Napieralski cyclization
  • glycosylation
  • natural products
  • polyketides
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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    Adachi, S., Watanabe, K., Iwata, Y., Kameda, S., Miyaoka, Y., Onozuka, M., Mitsui, R., Saikawa, Y., & Nakata, M. (2013). Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation. Angewandte Chemie - International Edition, 52(7), 2087-2091. https://doi.org/10.1002/anie.201209205