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

29 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

Fingerprint

Glycosylation
Cyclization
Polyketides
Cycloaddition
Palladium
Antibiotics
Sugars
Anti-Bacterial Agents
lactonamycin
lactonamycin Z

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Adachi, S., Watanabe, K., Iwata, Y., Kameda, S., Miyaoka, Y., Onozuka, M., ... 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

Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation. / Adachi, Satoshi; Watanabe, Kana; Iwata, Yusuke; Kameda, Shunsuke; Miyaoka, Yoshihito; Onozuka, Masao; Mitsui, Ryo; Saikawa, Yoko; Nakata, Masaya.

In: Angewandte Chemie - International Edition, Vol. 52, No. 7, 11.02.2013, p. 2087-2091.

Research output: Contribution to journalArticle

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, vol. 52, no. 7, pp. 2087-2091. https://doi.org/10.1002/anie.201209205
Adachi, Satoshi ; Watanabe, Kana ; Iwata, Yusuke ; Kameda, Shunsuke ; Miyaoka, Yoshihito ; Onozuka, Masao ; Mitsui, Ryo ; Saikawa, Yoko ; Nakata, Masaya. / Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation. In: Angewandte Chemie - International Edition. 2013 ; Vol. 52, No. 7. pp. 2087-2091.
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