Toward the total synthesis of luminamicin; An anaerobic antibiotic: Construction of highly functionalized cis-decalin containing a bridged ether moiety

Hiroyasu Ando, Aoi Kimishima, Motoyoshi Ohara, Tomoyasu Hirose, Takanori Matsumaru, Hirokazu Takada, Keisuke Morodome, Takehiro Miyamoto, Akihiro Sugawara, Satoshi Mura, Toshiaki Sunazuka

Research output: Contribution to journalArticle

Abstract

Synthesis of a cis-decalin moiety, containing an oxa-bridged cis-decalin ring system (11-oxatricyclo(5.3.1. 1,7 0 3,8)undecane), as a key intermediate of the total synthesis of luminamicin (1) was accomplished. One of the essential steps in our synthetic route is construction of a cis-decaline framework using a one-pot Michael addition-aldol reaction. Additionally, the bridged ether moiety was obtained by an intramolecular 1,6-oxa-Michael reaction of a conjugated aldehyde.

Original languageEnglish
Pages (from-to)268-272
Number of pages5
JournalJournal of Antibiotics
Volume71
Issue number2
DOIs
Publication statusPublished - 2018 Feb 1
Externally publishedYes

Fingerprint

Ether
Anti-Bacterial Agents
Aldehydes
luminamicin
decalin
3-hydroxybutanal
undecane

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Toward the total synthesis of luminamicin; An anaerobic antibiotic : Construction of highly functionalized cis-decalin containing a bridged ether moiety. / Ando, Hiroyasu; Kimishima, Aoi; Ohara, Motoyoshi; Hirose, Tomoyasu; Matsumaru, Takanori; Takada, Hirokazu; Morodome, Keisuke; Miyamoto, Takehiro; Sugawara, Akihiro; Mura, Satoshi; Sunazuka, Toshiaki.

In: Journal of Antibiotics, Vol. 71, No. 2, 01.02.2018, p. 268-272.

Research output: Contribution to journalArticle

Ando, H, Kimishima, A, Ohara, M, Hirose, T, Matsumaru, T, Takada, H, Morodome, K, Miyamoto, T, Sugawara, A, Mura, S & Sunazuka, T 2018, 'Toward the total synthesis of luminamicin; An anaerobic antibiotic: Construction of highly functionalized cis-decalin containing a bridged ether moiety', Journal of Antibiotics, vol. 71, no. 2, pp. 268-272. https://doi.org/10.1038/ja.2017.77
Ando, Hiroyasu ; Kimishima, Aoi ; Ohara, Motoyoshi ; Hirose, Tomoyasu ; Matsumaru, Takanori ; Takada, Hirokazu ; Morodome, Keisuke ; Miyamoto, Takehiro ; Sugawara, Akihiro ; Mura, Satoshi ; Sunazuka, Toshiaki. / Toward the total synthesis of luminamicin; An anaerobic antibiotic : Construction of highly functionalized cis-decalin containing a bridged ether moiety. In: Journal of Antibiotics. 2018 ; Vol. 71, No. 2. pp. 268-272.
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