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

1 Citation (Scopus)

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

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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    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, 71(2), 268-272. https://doi.org/10.1038/ja.2017.77