Regioselective (3 + 2) cycloaddition reactions of zerumbone: synthesis of isoxazolines and spiro-pyrrolizidino-oxindoles, conformational diversity and theoretical insights

Nandha Kumar Murthi, Naga Venkateswara Rao Nulakani, Mohamad Akbar Ali, Tanay Kundu and Pushparathinam Gopinath

Org. Biomol. Chem., 2025
DOI: 10.1039/D5OB00840A

How does cross-conjugation influence thiol additions to enones? A computational study of thiol trapping by the naturally occurring divinyl ketones zerumbone and α-santonin

Jonathan Y. C. Ting, Ras Baizureen Roseli and Elizabeth H. Krenske

Org. Biomol. Chem., 2020, 18, 1426
DOI: 10.1039/C9OB02709B

Attractive Reactivity of a Natural Product, Zerumbone

Takashi KITAYAMA

Bioscience, Biotechnology, and Biochemistry, 2011, 75, 199
DOI: 10.1271/bbb.100532

ChemInform Abstract: Selective Conjugate Addition to Zerumbone and Transannular Cyclization of Its Derivatives.

Kouichi Ohe, Koji Miki, Shin‐ichi Yanagi, Takumi Tanaka, Seiji Sawada and Sakae Uemura

ChemInform, 2001, 32
DOI: 10.1002/chin.200112181

Removal of the E-Olefin Barrier of Humulene Leading to Unnatural Terpenoid-like Skeletons

Takehiro Nishimura, Junya Kawai, Yoshiteru Oshima and Haruhisa Kikuchi

Org. Lett., 2018, 20, 7317
DOI: 10.1021/acs.orglett.8b03259

Putative Biomimetic Route to 8-Oxabicyclo[3.2.1]octane Motif from a Humulene Sesquiterpenoid Zerumbone

Kollery S. Veena, Greeshma Gopalan, Murali Madhukrishnan, Sunil Varughese, Kokkuvayil Vasu Radhakrishnan and Ravi S. Lankalapalli

Org. Lett., 2020, 22, 6409
DOI: 10.1021/acs.orglett.0c02220

The chemistry of zerumbone. Part 5: Structural transformation of the dimethylamine derivatives

Takashi Kitayama, Taketo Yokoi, Yasushi Kawai, Richard K Hill, Masanori Morita, Tadashi Okamoto, Yukio Yamamoto, Valery V Fokin, K.Barry Sharpless and Seiji Sawada

Tetrahedron, 2003, 59, 4857
DOI: 10.1016/S0040-4020(03)00667-7

Lewis‐Acid‐Catalyzed Activation of Zerumbone towards Sesquiterpenoid Derivatives: Sustainable Utilization of Abundant Natural Resources for the Synthesis of Chemically Diverse Architectures

Bhandara Purayil Dhanya, Greeshma Gopalan, Parameswaran Sasikumar, Sivadas Neethu, Murugan Thulasi Meenu, Puthiyaparambath Sharathna, Jubi John, Sunil Varughese, Mamiyil Sabu, Mathew Dan and Kokkuvayil Vasu Radhakrishnan

Asian J Org Chem, 2018, 7, 471
DOI: 10.1002/ajoc.201800006

Synthesis of New Zerumbone Hydrazones and Their In-vitro Anticancer Activity

Vu V. Vu and Tran K. Vu

CBC, 2021, 17, 331
DOI: 10.2174/1573407216999200630133625

Synthesis of a novel inhibitor against MRSA and VRE: Preparation from zerumbone ring opening material showing histidine-kinase inhibition

Takashi Kitayama, Risa Iwabuchi, Shu Minagawa, Seiji Sawada, Ryo Okumura, Kazuki Hoshino, John Cappiello and Ryutaro Utsumi

Bioorganic & Medicinal Chemistry Letters, 2007, 17, 1098
DOI: 10.1016/j.bmcl.2006.11.015

Unprecedented olefin-dependent histidine–kinase inhibitory of zerumbone ring-opening material

Takashi Kitayama, Risa Iwabuchi, Shu Minagawa, Fumihiro Shiomi, John Cappiello, Seiji Sawada, Ryutaro Utsumi and Tadashi Okamoto

Bioorganic & Medicinal Chemistry Letters, 2004, 14, 5943
DOI: 10.1016/j.bmcl.2004.08.071

Novel synthesis of zerumbone-pendant derivatives and their biological activity

Takashi Kitayama, Maki Nakahira, Kae Yamasaki, Hiromi Inoue, Chika Imada, Yuji Yonekura, Masataka Awata, Hikaru Takaya, Yasushi Kawai, Kohta Ohnishi and Akira Murakami

Tetrahedron, 2013, 69, 10152
DOI: 10.1016/j.tet.2013.09.026

Intramolecular OH⋅⋅⋅FC Hydrogen Bonding in Fluorinated Carbohydrates: CHF is a Better Hydrogen Bond Acceptor than CF2

Guy T. Giuffredi, Véronique Gouverneur and Bruno Bernet

Angew Chem Int Ed, 2013, 52, 10524
DOI: 10.1002/anie.201303766

The chemistry of Zerumbone IV

Takashi Kitayama, Ryuhei Nagao, Tomomi Masuda, Richard K. Hill, Masanori Morita, Masahiro Takatani, Seiji Sawada and Tadashi Okamoto

Journal of Molecular Catalysis B: Enzymatic, 2002, 17, 75
DOI: 10.1016/S1381-1177(02)00009-7

Kalparinol, a Salvialane (Isodaucane) Sesquiterpenoid Derived from Native Australian Dysphania Species That Suggests a Putative Biogenetic Link to Zerumbone

Yuen Ping Tan, Andrei I. Savchenko, Kylie A. Agnew-Francis, Glen M. Boyle, Paul V. Bernhardt, James A. Fraser and Craig M. Williams

J. Nat. Prod., 2020, 83, 1473
DOI: 10.1021/acs.jnatprod.9b01039

Remarkable synthesis and structure of allene type zerumbone

Takashi Kitayama, Tomomi Masuda, Kumi Sakai, Chika Imada, Yuji Yonekura and Yasushi Kawai

Tetrahedron, 2006, 62, 10859
DOI: 10.1016/j.tet.2006.08.102

Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

Mohanan Biji, Bernard Prabha, Ravi S. Lankalapalli and Kokkuvayil Vasu Radhakrishnan

The Chemical Record, 2021, 21, 3943
DOI: 10.1002/tcr.202100206

A Review on zerumbone and its semisynthetic Analogs: Synthesis and Implications in Medicinal chemistry

Murthi Nandha Kumar, Rambabu Dandela and Pushparathinam Gopinath

Bioorganic Chemistry, 2025, 154, 108074
DOI: 10.1016/j.bioorg.2024.108074

Remarkable Potential of Zerumbone to Generate a Library with Six Natural Product-like Skeletons by Natural Material-Related Diversity-Oriented Synthesis

Yoshimi Utaka, Gengo Kashiwazaki, Noriko Tsuchida, Miyuki Fukushima, Issei Takahashi, Yasushi Kawai and Takashi Kitayama

J. Org. Chem., 2020, 85, 8371
DOI: 10.1021/acs.joc.0c00689

Asymmetric synthesis of versatile monoepoxyzerumbone and monoepoxyzerumbol

Takashi Kitayama, Masataka Awata, Yasushi Kawai, Azusa Tsuji and Yasuhiko Yoshida

Tetrahedron: Asymmetry, 2008, 19, 2367
DOI: 10.1016/j.tetasy.2008.10.002

Intramolecular OH⋅⋅⋅FC Hydrogen Bonding in Fluorinated Carbohydrates: CHF is a Better Hydrogen Bond Acceptor than CF2

Guy T. Giuffredi, Véronique Gouverneur and Bruno Bernet

Angewandte Chemie, 2013, 125, 10718
DOI: 10.1002/ange.201303766

The chemistry of zerumbone. Part 3: Stereospecific creation of five stereogenic centers by double Sharpless oxidation

Takashi Kitayama, Tomomi Masuda, Yasushi Kawai, Richard K. Hill, Masahiro Takatani, Seiji Sawada and Tadashi Okamoto

Tetrahedron: Asymmetry, 2001, 12, 2805
DOI: 10.1016/S0957-4166(01)00505-5

Asymmetric synthesis of triepoxyzerumbol

Takashi Kitayama, Yasuhiko Yoshida, Jun-ichi Furukawa, Yasushi Kawai and Seiji Sawada

Tetrahedron: Asymmetry, 2007, 18, 1676
DOI: 10.1016/j.tetasy.2007.07.013

Zerumbone: Comprehensive Examination of the Scientific Literature

Siddig Ibrahim Abdelwahab, Manal Mohamed Elhassan T, Abdullah Farasani, Ahmed Ali Jerah, Ieman A. Aljahdali, Bassem Oraibi, Hassan Ahmad Alfaifi, Amal Hamdan Alzahrani, Omar Oraibi and Yasir Babiker

International J. of Pharmacology, 2024, 20, 768
DOI: 10.3923/ijp.2024.768.784

Synthesis of novel zerumbone derivatives via regioselective palladium catalyzed decarboxylative coupling reaction: a new class of α-glucosidase inhibitors

K.R. Ajish, B.P. Dhanya, Nayana Joseph, M. Priya Rani, K.G. Raghu, V.P. Vineetha and K.V. Radhakrishnan

Tetrahedron Letters, 2014, 55, 665
DOI: 10.1016/j.tetlet.2013.11.110

Elucidation of the Sharpless epoxidation of zerumbol

Takashi Kitayama, Atsushi Furuya, Chiyuki Moriyama, Tomomi Masuda, Sachiko Fushimi, Yuji Yonekura, Haruko Kubo, Yasushi Kawai and Seiji Sawada

Tetrahedron: Asymmetry, 2006, 17, 2311
DOI: 10.1016/j.tetasy.2006.06.049

Metal‐Free trans‐Aziridination of Zerumbone: Synthesis and Biological Evaluation of Aziridine Derivatives of Zerumbone

Greeshma Gopalan, Bhandara Purayil Dhanya, Jayaram Saranya, Thankappan Remadevi Reshmitha, Thekke Veettil Baiju, Murugan Thulasi Meenu, Mangalam S. Nair, Prakasan Nisha and Kokkuvayil Vasu Radhakrishnan

Eur J Org Chem, 2017, 2017, 3072
DOI: 10.1002/ejoc.201700410