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

• DOI: 10.1038/ja.2017.77
• Publication Date: 2017-07-05T10:07:40Z
• Authors: Hiroyasu Ando; Aoi Kimishima; Motoyoshi Ohara; Tomoyasu Hirose; Takanori Matsumaru; Hirokazu Takada; Keisuke Morodome; Takehiro Miyamoto; Akihiro Sugawara; Satoshi Ōmura; Toshiaki Sunazuka
• Keywords: Moiety; Decalin; Aldol reaction; Undecane; Michael reaction; Silyl ether

Synthesis of a cis-decalin moiety, containing an oxa-bridged cis-decalin ring system (11-oxatricyclo(5.3.1.1,703,8)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.