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Synthesis
DOI: 10.1055/a-2770-4634
Paper

Total Synthesis of Keramaphidin B and Ingenamine

Autor*innen

  • Yuki Kurihara

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Minori Yagi

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Sho Yoshimura

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Kenta Ito

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Yuta Shimotani

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Miyuna Uematsu

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Takashi Noguchi

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Haruka Yasufuku

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Ayane Okita

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Keisuke Fukaya

    2   Department of Biotechnology, Toyama Prefectural University, Imizu, Japan (Ringgold ID: RIN57948)

  • Takeshi Oishi

    3   School of Medicine, Keio University School of Medicine Graduate School of Medicine, Yokohama, Japan (Ringgold ID: RIN38084)

  • Ryota Kawahara

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Siro Simizu

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Noritaka Chida

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Toshitaka Okamura

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

  • Takaaki Sato 

    1   Department of Applied Chemistry, Keio University Faculty of Science and Technology Graduate School of Science and Technology, Yokohama, Japan (Ringgold ID: RIN74013)

Gefördert durch: The Japan Science Society Sasakawa Scientific Research Grant
Gefördert durch: MEXT 22H02084,22H05375,24H01090
Gefördert durch: JST SPRING JPMJSP2123
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The full details of the total synthesis of keramaphidin B and ingenamine are reported. The most conspicuous transformation in our total synthesis is the base-catalyzed Diels-Alder reaction using dynamic regioselective crystallization (alternatively referred to as crystallizationinduced transformation: CIT). The tertiary alcohol, which is used for the base-catalyzed activation in the Diels-Alder reaction, is removed as its p-fluorobenzoate using SmI 2 (HMPA) 4 . Double macrocyclic alkylation enables the regioselective construction of two macrocycles in a single step. The developed sequence is highly efficient, achieving the unified total synthesis of keramaphidin B and ingenamine within 13 steps from commercially available compounds. Our biological study elucidated the significant role of the two macrocycles in their antiproliferative effects against human cancer cell lines.



Publikationsverlauf

Eingereicht: 21. November 2025

Angenommen: 10. Dezember 2025

Accepted Manuscript online:
11. Dezember 2025

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