Laboratory of Organic Chemistry

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Original Paper

Synthesis of Ozonides Mediated by Molecular Sieve Under Solvent-Free Conditions
El-kholany, R. M.; Kishimoto, N.; Tanaka, K.; Takamura, H.; Kadota, I. Tetrahedron 2024, 165, 134137.

Total synthesis and structure–antifouling activity relationship of scabrolide F
Takamura, H.; Sugitani, Y.; Morishita, R.; Yorisue, T.; Kadota, I. Org. Biomol. Chem. 2024, 22, 5739-5747.
[selected as cover picture]
[press released at Okayama University]

Strongly reducing helical phenothiazines as recyclable organophotoredox catalysts
Ando, H.; Takamura, H.; Kadota, I.; Tanaka, K. Chem. Commun. 2024, 60, 4765-4768.

[selected as cover picture]
[press release at Okayama University]

Efficient Method for the Preparation of Ozonides Under Dry Conditions
El-kholany, R. M.; Kishimoto, N.; Tanaka, K.; Takamura, H.; Kadota, I. Bull. Chem. Soc. Jpn. 2023, 96, 1316-1318.

Relative stereochemical determination of the C61–C83 fragment of symbiodinolide using a stereodivergent synthetic approach
Takamura, H.; Hattori, K.; Ohashi, T.; Otsu, T.; Kadota, I. Org. Biomol. Chem. 2023, 21, 8837–8848. [selected as cover picture]


Chemical synthesis and antifouling activity of monoterpene–furan hybrid molecules
Takamura, H.; Kinoshita, Y.; Yorisue, T.; Kadota, I. Org. Biomol. Chem. 2023, 21, 632–638.


Total Synthesis of Scabrolide F
Takamura, H.; Sugitani, Y.; Morishita, R.; Kadota, I. Org. Lett. 2022, 24, 7845-7849.

Chemical Synthesis and Biological Effect on Xylem Formation of Xylemin and Its Analogues
Takamura, H.; Motose,H.; Otsu, T.; Shinohara,S.; Kouno, R.; Kadota, I.; Takahashi, T. Eur. J. Org. Chem. 2020, 2745–2753

Concise Synthesis of Anticancer Active trans-4-(4-Octylphenyl)prolinol
Ando, J.; Tazawa, A.; Ishizawa, K.; Tanaka, M.; Takamura, H. Heterocycles 2019, 99, 716–723.

Stereodivergent and Stereoselective Synthesis of cis- and trans-4-Substituted Prolinols
Ando, J.; Tazawa, A.; Ishizawa, K.; Tanaka, M.; Takamura, H. Heterocycles 2019, 99, 188–199.

Stereocontrolled Synthesis of the Macrolactone Core of Neopeltolide
Meissner, A.; Tanaka, N.;Takamura, H.; Kadota, I. Tetrahedron Lett. 2019, 60, 432-434.

Total Synthesis of Rhoiptelol B
Tanaka, N.; Takamura, H.; Kadota, I. Heterocycles, 2018, 97, 1157-1164.

Formal Total Synthesis of Enigmazole A
Meissner, A.; Kishi,T.; Fujisawa, Y.; Murai, Y.;Takamura, H.; Kadota, I. Tetrahedron Lett. 2018, 59, 4492-4495.

Unified Total Synthesis, Stereostructural Elucidation, and Biological Evaluation of Sarcophytonolides
Takamura, H.; Kikuchi, T.; Iwamoto, K.; Nakao, E.; Harada, N.; Otsu, T.; Endo, N.; Fukuda, Y.; Ohno, O.; Suenaga, K.; Guo, Y.-W.; Kadota, I. J. Org. Chem. 2018, 83, 11028–11056.

Improved Synthesis of the A–E Ring Segment of Ciguatoxin CTX3C by Using Intramolecular Allylations
Tanaka, T.; Asakura, H.; Fujiwara, R.; Kumamoto, K.; Izuka, H.; Shiroma, K.; Takamura, H.; Kadota, I. Bull. Chem. Soc. Jpn. 2018, 91, 507–514.

Convegent Total Synthesis of (-)-Dactylolide
Tanaka, T.; Murai, Y.; Kishi, T.; Takamura, H.; Kadota, I. Tetrahedron Lett. 2018, 59, 763-766.

Total Synthesis of Two Possible Diastereomers of Natural 6-Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation
Takamura, H.; Katsube, T.; Okamoto, K.; Kadota, I. Chem. Eur. J. 2017, 23, 17191–17194.

Late-stage Divergent Synthesis and Antifouling Activity of Geraniol–butenolide Hybrid Molecules
Takamura, H,; Ohashi, T.; Kikuchi, T.; Endo, N,; Fukuda, Y.; Kadota, I. Org. Biomol. Chem. 2017, 15, 5549-5555.

Total Synthesis of Sarcophytonolide H and Isosarcophytonolide D: Structural Revision of Isosarcophytonolide D and Structure–Antifouling Activity Relationship of Sarcophytonolide H
Takamura, H.; Kikuchi, T.; Endo, N.; Fukuda, Y.; Kadota, I. Org. Lett. 2016, 18, 2110–2113

Chemical Control of Xylem Differentiation by Thermospermine, Xylemin, and Auxin
Yoshimoto, K.; Takamura, H.; Kadota, I.; Motose, H.; Takahashi, T. Sci. Rep. 2016, 6, 21487. [press release at Okayama University]

Stereodivergent Synthesis and Stereochemical Reassignment of the C79–C104 Fragment of Symbiodinolide
Takamura, H.; Fujiwara, T.; Kawakubo, Y.; Kadota, I.; Uemura, D. Chem. Eur. J. 2016, 22, 1984–1996. [selected as VIP and cover picture]

Stereoselective Synthesis of the Proposed C79–C104 Fragment of Symbiodinolide
Takamura, H.; Fujiwara, T.; Kawakubo, Y.; Kadota, I.; Uemura, D. Chem. Eur. J. 2016, 22, 1979–1983. [selected as VIP and highlighted in ChemistryViews website]

Covergent Synthesis of the EFGH Ring System of Ciguatoxin CTX3C
Kadota, I.; Sato, Y.; Fujita, N.; Takamura, H.; Yamamoto, Y. Tetrahedron 2015, 71, 6547–6558.

Stereodivergent Synthesis and Relative Stereostructure of the C1–C13 Fragment of Symbiodinolide
Takamura, H.; Wada, H.; Ogino, M.; Kikuchi, T.; Kadota, I.; Uemura, D. J. Org. Chem. 2015, 80, 3111–3123.

Stereocontrolled Synthesis of the C1–C17 Fragment of Enigmazole A
Kishi, T.; Fujisawa, Y.; Takamura, H.; Kadota, I. Heterocycles 2014, 89, 515–522.

Improved Synthesis of the A–E Ring Segment of Ciguatoxin CTX3C
Shiroma, K.; Asakura, H.; Tanaka, T.; Takamura, H.; Kadota, I. Heterocycles 2014, 88, 969–973.

Stereoselective Synthesis of the C79–C97 Fragment of Symbiodinolide 
Takamura, H.; Fujiwara, T.; Kadota, I.; Uemura, D. Beilstein J. Org. Chem. 2013, 9, 1931–1935.

Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Structural Elucidation
Takamura, H.; Iwamoto, K.; Nakao, E.; Kadota, I. Org. Lett. 2013, 15, 1108–1111.

Total Synthesis, Structural Elucidation, and Structure–Cytotoxic Activity Relationship of (–)-Gummiferol
Takamura, H.; Wada, H.; Lu, N.; Ohno, O.; Suenaga, K.; Kadota, I. J. Org. Chem. 2013, 78, 2443–2454.

Synthesis of the E Ring Segment of Ciguatoxin CTX3C via the Negishi Coupling of Cyclic Ketene Acetal Triflate
Shiroma, K.; Takamura, H.; Kadota, I. Heterocycles 2012, 86, 997–1001.

Stereoselective Synthesis of the C94–C104 Fragment of Symbiodinolide
Takamura, H.; Tsuda, K.; Kawakubo, Y.; Kadota, I.; Uemura, D. Tetrahedron Lett. 2012, 53, 4317–4319.

A Convergent Synthesis of the Right-hand Fragment of Ciguatoxin CTX3C
Takamura, H.; Abe, T.; Nishiuma, N.; Fujiwara, R.; Tsukeshiba, T.; Kadota, I. Tetrahedron2012, 68, 2245–2260.

Convergent Synthesis of the HIJKLM Ring System of Ciguatoxin CTX3C
Takamura, H.; Nishiuma, N.; Abe, T.; Kadota, I. Org. Lett. 2011, 13, 4704–4707.

Total Synthesis and Absolute Configuration of (–)-Gummiferol
Takamura, H.; Wada, H.; Lu, N.; Kadota, I. Org. Lett. 2011, 13, 3644–3647.


Stereocontrolled Synthesis and Structural Confirmation of the C14–C24 Degraded Fragment of Symbiodinolide
Takamura, H.; Kadonaga, Y.; Kadota, I.; Uemura, D. Tetrahedron 2010, 66, 7569–7576.

Total Synthesis of Brevenal
Takamura, H.; Yamagami, Y.; Kishi, T.; Kikuchi, S.; Nakamura, Y.; Kadota, I.; Yamamoto, Y. Tetrahedron 2010, 66, 5329–5344.

A New Method for the Stereoselective Construction of Angular Methyl Group of Fuzed Cyclic Ethers
Kadota, I.; Kishi, T.; Fujisawa, Y.; Yamagami, Y.; Takamura, H. Tetrahedron Lett. 2010, 51, 3960–3961.

Stereoselective Synthesis of the C14–C24 Degraded Fragment of Symbiodinolide
Takamura, H.; Kadonaga, Y.; Kadota, I.; Uemura, D. Tetrahedron Lett. 2010, 51, 2603–2605.

Stereoselective Synthesis and Absolute Configuration of the C1’–C25’ Fragment of Symbiodinolid
Takamura, H.; Murata, T.; Asai, T.; Kadota, I.; Uemura, D. J. Org. Chem. 2009, 74, 6658–6666.


Convergent Synthesis of the A–E Ring Segment of Ciguatoxin CTX3C
Kadota, I.; Abe, T.; Uni, M.; Takamura, H.; Yamamoto, Y. Tetrahedron 2009, 65, 7784–7789.

Stereoselective Synthesis and Absolute Configuration of the C33–C42 Fragment of Symbiodinolide
Takamura, H.; Kadonaga, Y.; Yamano, Y.; Han, C.; Kadota, I.; Uemura, D. Tetrahedron 2009, 65, 7449–7456.

Selective Cleavage of Primary MPM Ethers with TMSI/Et3N
Kadota, I.; Yamagami, Y.; Fujita, N.; Takamura, H. Tetrahedron Lett. 2009, 50, 4552–4553.

Synthesis and Structural Revision of Symbiodinolide C23–C34 Fragment
Murata, T.; Sano, M.; Takamura, H.; Kadota, I.; Uemura, D. J. Org. Chem. 2009, 74, 4797–4803.

Total Synthesis of Brevenal
Takamura, H.; Kikuchi, S.; Nakamura, Y.; Yamagami, Y.; Kishi, T.; Kadota, I.; Yamamoto, Y. Org. Lett. 2009, 11, 2531–2534. [highlighted in Synfacts 2009, 1184.]

Synthesis and Structural Determination of the C33–C42 Fragment of Symbiodinolide
Takamura, H.; Kadonaga, Y.; Yamano, Y.; Han, C.; Aoyama, Y.; Kadota, I.; Uemura, D. Tetrahedron Lett. 2009, 50, 863–866.

A Transannular Diels–Alder Strategy to the Construction of the CDE Ring System of Nakiterpiosin
Takamura, H.; Yamagami, Y.; Ito, T.; Ito, M.; Arimoto, H.; Kadota, I.; Uemura, D. Heterocycles 2009, 77, 351–364.

Stereocontrolled Synthesis of the C79–C96 Fragment of Symbiodinolide
Takamura, H.; Ando, J.; Abe, T.; Murata, T.; Kadota, I.; Uemura, D. Tetrahedron Lett. 2008, 49, 4626–4629.

A Cross–Metathesis Approach to the Stereocontrolled Synthesis of the AB Ring Segment of Ciguatoxin
Kadota, I.; Abe, T.; Uni, M.; Takamura, H.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 3643–3647.

Formal Total Synthesis of Hemibrevetoxin B via the Intramolecular Allylation Followed by Ring-closing Metathesis
Kadota, I.; Abe, T.; Ishitsuka, Y.; Touchy, A. S.; Nagata, R.; Yamamoto, Y. Heterocycles 2007, 74, 617-627.

Solvent-Controlled Stereoselective Formation of a Cyclic Ether in the Lewis Acid-Mediated Allylation of an α-Chloroacetoxy Acyclic Ether. Very High Stereoselectivity in CH3CN vs Low Stereoselectivity in CH2Cl2
Gridnev, I. D.; Kikuchi, S.; Touchy, A. S.; Kadota, I.; Yamamoto, Y. J. Org. Chem. 2007, 72, 8371-8375.

A Convergent Approach to the Formal Total Synthesis of Hemibrevetoxin B
Kadota, I.; Abe, T.; Ishitsuka, Y.; Touchy, A. S.; Nagata, R.; Yamamoto, Y. Tetrahedron Lett. 2006, 48, 219-221. 

   
 
Review and Book  
Takamura, H. Chapter 9: Synthetic Approach Toward Structural Elucidation of Marine Natural Product Symbiodinolide. In New Tide of Natural Product Chemistry, First Edition; Ishikawa, H.; Takayama, H., Ed.; Springer Nature Singapore Pte Ltd.: Singapore, 2023; pp. 179–210.

Takamura, H.; Kadota, I.
Protecting-Group-Free Synthesis of Natural Products and Analogs, Part II. In Protecting- Group-Free Organic Synthesis: Improving Economy and Efficiency, First Edition
Fernandes, R. A., Ed.; John Wiley & Sons Ltd.: Hoboken, NJ, 2018; pp 59–86.

Recent Topics of the Stereodivergent Synthesis of Natural Products
Takamura, H. Tetrahedron Lett. 2018, 59, 955-966.