@article{ae150d2894c74c0f92a4d30930ac4d6f,
title = "Total Syntheses and Determination of Absolute Configurations of Cep-212 and Cep-210, Predicted Biosynthetic Intermediates of Tetrodotoxin Isolated from Toxic Newt",
abstract = "Total syntheses of Cep-212 and Cep-210, predicted biosynthetic intermediates of tetrodotoxin isolated from the Japanese toxic newt, have been accomplished from geraniol by an intramolecular hetero Diels-Alder reaction as a key step in a highly stereoselective manner. The success of these syntheses enabled us to determine their absolute configurations by using a chiral normal-phase HPLC/MS analysis of the bis-dinitrobenzene derivative of natural Cep-212 and reference derivatives prepared from chemically synthesized enantiomers.",
author = "Masaatsu Adachi and Tadachika Miyasaka and Yuta Kudo and Keita Sugimoto and Mari Yotsu-Yamashita and Toshio Nishikawa",
note = "Funding Information: This work was financially supported by JSPS KAKENHI Grants-in-Aid for Scientific Research (B) (16H04915) and (C) (15K07410, 18K05456), a Grant-in-Aid for Challenging Exploratory Research (17K19195), and a Grant-in-Aid for Scientific Research on Innovative Area “Frontier Research on Chemical Communications” (17H06406) from MEXT, Japan, and Shorai Foundation for Science and Technology. T.M. is grateful for a Nagoya University Graduate School of Bioagricultural Sciences “Mizutani Scholarship”. We thank Prof. K. Nakagawa and Dr. J. Ito (Tohoku University) for help with the chiral HPLC/MS analysis. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",
year = "2019",
month = feb,
day = "1",
doi = "10.1021/acs.orglett.8b04043",
language = "English",
volume = "21",
pages = "780--784",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "3",
}