Short Synthesis of (+)-Cylindricine C by Using a Catalytic Asymmetric Michael Reaction with a Two-Center Organocatalyst†
Tomoyuki Shibuguchi
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorHisashi Mihara
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorAkiyoshi Kuramochi
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorShun Sakuraba
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorTakashi Ohshima Dr.
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorMasakatsu Shibasaki Prof. Dr.
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorTomoyuki Shibuguchi
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorHisashi Mihara
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorAkiyoshi Kuramochi
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorShun Sakuraba
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorTakashi Ohshima Dr.
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorMasakatsu Shibasaki Prof. Dr.
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Fax: (+81) 3-5684-5206
Search for more papers by this authorThis work was supported by RFTF, a Grant-in-Aid for the Encouragement of Young Scientists (A), and a Grant-in-Aid for Specially Promoted Research from the Japan Society for the Promotion of Science (JSPS) and the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
Graphical Abstract
Two for the price of one: The total synthesis of (+)-cylindricine C has been achieved in six steps using a catalytic asymmetric Michael reaction and tandem cyclization. A newly designed two-center organocatalyst gives good selectivity in this Michael reaction. TaDiAS=tartrate-derived diammonium salt.
Supporting Information
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