HETEROCYCLES
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Obituary
Zenichi Yoshida (1925-2023)
Zenichi Yoshida (1925-2023)
Professor. Zenichi Yoshida,
a member of the Honorary Advisors of HETEROCYCLES (1975-1998),
has passed away on May 4, 2023 at the age of 97.
I deeply express my regret over his death.
Kunio Ogasawara
Editor
May 11, 2023
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December 24, 2019
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e-Journal
Abstract
1 data found. 1 - 1 listed
Paper | Regular issue | Vol 98, No. 11, 2019, pp. 1525 - 1535
Published online: 14th November, 2019
PDF (697KB)PDF with Links (667KB)
Published online: 14th November, 2019
DOI: 10.3987/COM-19-14171
■ Piperidine and Azetidine Formation by Direct Cyclization of Diols with N-Nonsubstituted Sulfonamide under the Mitsunobu Conditions Utilizing (Cyanomethylene)tributylphosphorane (CMBP) and Its Application to the Synthesis of Lupinine
Hiroto Kaku,* Yuhei Sonoda, Hideyuki Hishida, Yuri Taniguchi, Akiko Kubo, Takumi Hamaguchi, Mitsuyo Horikawa, Makoto Inai, Kei Kitamura, and Tetsuto Tsunoda*
*Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-machi, Tokushima, 770-8514, Japan
Abstract
(Cyanomethylene)tributylphosphorane (CMBP) can promote the Mitsunobu reaction of 1,3- and 1,5-diols with N-nonsubstituted sulfonamides, such as tosylamide (TsNH2) and 3,3-dimethoxypropylsulfonamide (DimpsNH2), to prepare azetidine and piperidine ring systems directly. Utilizing this methodology, lupinine, a biologically active piperidine alkaloid, was synthesized.
1 data found. 1 - 1 listed
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