Abstract
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.
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Acknowledgements
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.
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Dedicated to Professor KC Nicolaou and his outstanding contributions to complex natural product total synthesis and chemical biology.
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Ando, H., Kimishima, A., Ohara, M. et al. Toward the total synthesis of luminamicin; an anaerobic antibiotic: construction of highly functionalized cis-decalin containing a bridged ether moiety. J Antibiot 71, 268–272 (2018). https://doi.org/10.1038/ja.2017.77
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DOI: https://doi.org/10.1038/ja.2017.77
