2024-03-28T09:38:24Z
https://nagoya.repo.nii.ac.jp/oai
oai:nagoya.repo.nii.ac.jp:00024928
2023-01-16T04:14:14Z
643:666:667
De Novo Synthesis of Possible Candidates for the Inagami–Tamura Endogenous Digitalis-like Factor
Nakazaki, Atsuo
Hashimoto, Keiko
Ikeda, Ai
Shibata, Takahiro
Nishikawa, Toshio
open access
“This document is the Accepted Manuscript version of a Published Work that appeared in final form in [The Journal of Organic Chemistry], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [http://pubs.acs.org/articlesonrequest/AOR-4SXiUUWhVWXaJhUPs93D].”
De novo synthesis of possible candidates for the Inagami–Tamura endogenous digitalis-like factor (EDLF) was achieved to validate a previously proposed structure. Our synthetic approach involves a highly regio- and diastereoselective Mizoroki–Heck reaction and a Friedel–Crafts-type cyclodehydration to construct steroidal tetracycle 14 as a versatile common intermediate leading to seven 2,14β-dihydroxyestradiol analogues 1a–c, 2a–c, and 3 as possible candidates. By comparing the potency of inhibitory activity against Na+/K+-ATPase between the synthesized candidates and the EDLF, it was found that the proposed structure is not likely to be a true structure of the Inagami–Tamura EDLF.
ACS Publications
2017-09
eng
journal article
AM
http://hdl.handle.net/2237/27149
https://nagoya.repo.nii.ac.jp/records/24928
https://doi.org/10.1021/acs.joc.7b01640
0022-3263
The Journal of Organic Chemistry
82
17
9097
9111
https://nagoya.repo.nii.ac.jp/record/24928/files/revised_manuscript.pdf
application/pdf
609.3 kB
2018-09-01