Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113

Hiroyuki Sakauchi, Emi Higashi, Yuko Shimizu, Mikiko Kojima, Yuko Asamitsu, Shigefumi Kuwahara, Minoru Izumi, Hiromasa Kiyota

Research output: Contribution to journal › Article

Abstract

The spiroacetal [C(9)-C(20)] fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113, were prepared from a known bromo alcohol derived from (S)-citronellal, using thermodynamically controlled iodolactonization and spiroacetalization as the key steps.

Original languageEnglish
Pages (from-to)337-343
Number of pages7
JournalHeterocyclic Communications
Volume21
Issue number6
DOIs
Publication statusPublished - Dec 1 2015

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Alcohols
Anti-Bacterial Agents
citronellal

Keywords

  • acetylide
  • antibiotics
  • iodolactonization
  • selenolactonization
  • spiroacetalization
  • spirofungins A and B
  • Streptomyces violaceusniger Tü 4113
  • synthesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113. / Sakauchi, Hiroyuki; Higashi, Emi; Shimizu, Yuko; Kojima, Mikiko; Asamitsu, Yuko; Kuwahara, Shigefumi; Izumi, Minoru; Kiyota, Hiromasa.

In: Heterocyclic Communications, Vol. 21, No. 6, 01.12.2015, p. 337-343.

Research output: Contribution to journal › Article

Sakauchi, H, Higashi, E, Shimizu, Y, Kojima, M, Asamitsu, Y, Kuwahara, S, Izumi, M & Kiyota, H 2015, 'Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113', Heterocyclic Communications, vol. 21, no. 6, pp. 337-343. https://doi.org/10.1515/hc-2015-0193
Sakauchi H, Higashi E, Shimizu Y, Kojima M, Asamitsu Y, Kuwahara S et al. Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113. Heterocyclic Communications. 2015 Dec 1;21(6):337-343. https://doi.org/10.1515/hc-2015-0193
Sakauchi, Hiroyuki ; Higashi, Emi ; Shimizu, Yuko ; Kojima, Mikiko ; Asamitsu, Yuko ; Kuwahara, Shigefumi ; Izumi, Minoru ; Kiyota, Hiromasa. / Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113. In: Heterocyclic Communications. 2015 ; Vol. 21, No. 6. pp. 337-343.
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