TY - JOUR
T1 - Toward the total synthesis of luminamicin; An anaerobic antibiotic
T2 - Construction of highly functionalized cis-decalin containing a bridged ether moiety
AU - Ando, Hiroyasu
AU - Kimishima, Aoi
AU - Ohara, Motoyoshi
AU - Hirose, Tomoyasu
AU - Matsumaru, Takanori
AU - Takada, Hirokazu
AU - Morodome, Keisuke
AU - Miyamoto, Takehiro
AU - Sugawara, Akihiro
AU - Mura, Satoshi
AU - Sunazuka, Toshiaki
N1 - Funding Information:
This work was supported by Japan Society for the Promotion of Science (JSPS) KAKENHI Grants (numbers 16K08175, 26860015, 24790022 and 22890175) (AS); a Meiji Seika Pharma Award in Synthetic Organic Chemistry Japan (AS); a Kitasato University Research Grant for Young Researchers (AS), JSPS Research Fellowships for Young Scientists (TM and AK) and a Uehara Memorial foundation grant (TH). We also thank Dr K Nagai and Ms N Sato (School of Pharmacy, Kitasato University) for their analyses of mass and NMR spectra.
Publisher Copyright:
© 2018 Japan Antibiotics Research Association All rights reserved.
PY - 2018/2/1
Y1 - 2018/2/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85041202720&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85041202720&partnerID=8YFLogxK
U2 - 10.1038/ja.2017.77
DO - 10.1038/ja.2017.77
M3 - Article
C2 - 28676718
AN - SCOPUS:85041202720
SN - 0021-8820
VL - 71
SP - 268
EP - 272
JO - Journal of Antibiotics
JF - Journal of Antibiotics
IS - 2
ER -