Synthesis of the oxa-bridged octalin system of two anti-anaerobe antibiotics, luminamicin and lustromycin

Toshiaki Sunazuka, Masaki Handa, Tomoyasu Hirose, Takanori Matsumaru, Yuko Togashi, Kaoru Nakamura, Yuzuru Iwai, Satoshi Omura

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

An efficient, stereocontrolled entry to the 11-oxatricyclo[5.3.1.1,703,8]undecane nucleus of luminamicin and lustromycin was afforded via intramolecular hetero-Michael addition of enone 7 followed by intramolecular aldol condensation of aldehyde 5 by way of the epimerization at the stereocenter attached by the aldehyde group.

Original languageEnglish
Pages (from-to)5297-5300
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number30
DOIs
Publication statusPublished - 2007 Jul 23
Externally publishedYes

Fingerprint

Aldehydes
Anti-Bacterial Agents
Condensation
luminamicin
lustromycin
undecane
3-hydroxybutanal

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of the oxa-bridged octalin system of two anti-anaerobe antibiotics, luminamicin and lustromycin. / Sunazuka, Toshiaki; Handa, Masaki; Hirose, Tomoyasu; Matsumaru, Takanori; Togashi, Yuko; Nakamura, Kaoru; Iwai, Yuzuru; Omura, Satoshi.

In: Tetrahedron Letters, Vol. 48, No. 30, 23.07.2007, p. 5297-5300.

Research output: Contribution to journalArticle

Sunazuka, T, Handa, M, Hirose, T, Matsumaru, T, Togashi, Y, Nakamura, K, Iwai, Y & Omura, S 2007, 'Synthesis of the oxa-bridged octalin system of two anti-anaerobe antibiotics, luminamicin and lustromycin', Tetrahedron Letters, vol. 48, no. 30, pp. 5297-5300. https://doi.org/10.1016/j.tetlet.2007.05.104
Sunazuka, Toshiaki ; Handa, Masaki ; Hirose, Tomoyasu ; Matsumaru, Takanori ; Togashi, Yuko ; Nakamura, Kaoru ; Iwai, Yuzuru ; Omura, Satoshi. / Synthesis of the oxa-bridged octalin system of two anti-anaerobe antibiotics, luminamicin and lustromycin. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 30. pp. 5297-5300.
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