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  • Hiroyoshi Takamura

Synthesis and Evaluation of Natural Products and Biologically Active Molecules

Hiroyoshi Takamura

Hiroyoshi Takamura

Assoc. Professor

CONTACT INFO

RESEARCH INTERESTS

  • Synthetic Organic Chemistry
  • Natural Product
  • Biologically Active Molecule

ACHIEVEMENTS

Education

  • 2000 B.Sc., Department of Chemistry, Faculty of Science, Tohoku University
  • 2005 Ph.D., Department of Chemistry, Graduate School of Science, Tohoku University (Prof. Yoshinori Yamamoto lab.)

Academic Career

  • 2005–2007 Assistant Professor, Department of Chemistry, Graduate School of Science, Nagoya University (Prof. Daisuke Uemura lab.)
  • 2007–2015 Assistant Professor, Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
  • 2015–present Associate Professor, Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University

Honors and Fellowships

  • 2016 Top 10 Best Reviewer 2015 for Tetrahedron Journal
  • 2011 Shionogi Award in Synthetic Organic Chemistry, Japan
  • 2007 Presentation Award of 47th Symposium on the Chemistry of Natural Products
  • 2003–2005 Research Fellow of the Japan Society for the Promotion of Science
  • 2003 Student Presentation Award 2003 of the Chemical Society of Japan

Research Interests

Synthetic Organic Chemistry, Natural Product Synthesis

Publication

2023

  1. "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, DOI:10.1039/d3ob01420g.
  2. "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.

2022

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

2020

  1. "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.

2019

  1. "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.
  2. "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.
  3. "Stereocontrolled Synthesis of the Macrolactone Core of Neopeltolide" Meissner, A.; Tanaka, N.; Takamura, H.; Kadota, I. Tetrahedron Lett. 2019, 60, 432–434.

2018

  1. "Total Synthesis of Rhoiptelol B" Tanaka, N.; Takamura, H.; Kadota, I. Heterocycles 2018, 97, 1157–1164.
  2. "Formal Total Synthesis of Enigmazole A" Meissner, A.; Kishi, T.; Fujisawa, Y.; Murai, Y.; Takamura, H.; Kadota, I. Tetrahedron Lett. 2018, 59, 4492–4495.
  3. "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.
  4. "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.
  5. "Recent Topics of the Stereodivergent Synthesis of Natural Products" Takamura, H. Tetrahedron Lett. 2018, 59, 955–966. (review)
  6. "Convergent Total Synthesis of (–)-Dactylolide" Tanaka, T.; Murai, Y.; Kishi, T.; Takamura, H.; Kadota, I. Tetrahedron Lett. 2018, 59, 763–766.

2017

  1. "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.
  2. "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.

2016

  1. "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.
  2. "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]
  3. "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]
  4. "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]

2015

  1. "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.
  2. "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.

2014

  1. "Stereocontrolled Synthesis of the C1–C17 Fragment of Enigmazole A" Kishi, T.; Fujisawa, Y.; Takamura, H.; Kadota, I. Heterocycles 2014, 89, 515–522.
  2. "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.

2013

  1. "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.
  2. "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.
  3. "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.

2012

  1. "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.
  2. "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.
  3. "A Convergent Synthesis of the Right-Hand Fragment of Ciguatoxin CTX3C" Takamura, H.; Abe, T.; Nishiuma, N.; Fujiwara, R.; Tsukeshiba, T.; Kadota, I. Tetrahedron 2012, 68, 2245–2260.

2011

  1. "Convergent Synthesis of the HIJKLM Ring System of Ciguatoxin CTX3C" Takamura, H.; Nishiuma, N.; Abe, T.; Kadota, I. Org. Lett. 2011, 13, 4704–4707.
  2. "Total Synthesis and Absolute Configuration of (–)-Gummiferol" Takamura, H.; Wada, H.; Lu, N.; Kadota, I. Org. Lett. 2011, 13, 3644–3647.

2010

  1. "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.
  2. "Total Synthesis of Brevenal" Takamura, H.; Yamagami, Y.; Kishi, T.; Kikuchi, S.; Nakamura, Y.; Kadota, I.; Yamamoto, Y. Tetrahedron 2010, 66, 5329–5344.
  3. "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.
  4. "Stereoselective Synthesis of the C14–C24 Degraded Fragment of Symbiodinolide" Takamura, H.; Kadonaga, Y.; Kadota, I.; Uemura, D. Tetrahedron Lett. 2010, 51, 2603–2605.

2009

  1. "Stereoselective Synthesis and Absolute Configuration of the C1’–C25’ Fragment of Symbiodinolide" Takamura, H.; Murata, T.; Asai, T.; Kadota, I.; Uemura, D. J. Org. Chem. 2009, 74, 6658–6666.
  2. "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.
  3. "Determination of Absolute Configuration of C14–C23 Fragment in Symbiodinolide" Han, C.; Yamano, Y.; Kita, M.; Takamura, H.; Uemura, D. Tetrahedron Lett. 2009, 50, 5280–5282.
  4. "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.
  5. "Selective Cleavage of Primary MPM Ethers with TMSI/Et3N" Kadota, I.; Yamagami, Y.; Fujita, N.; Takamura, H. Tetrahedron Lett. 2009, 50, 4552–4553.
  6. "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.
  7. "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.]
  8. "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.
  9. "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.

2008

  1. "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.
  2. "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.

2007

  1. "Concise Synthesis of a Highly Functionalized Cyclopentane Segment: Toward the Total Synthesis of Kansuinine A" Shimokawa, K.; Takamura, H.; Uemura, D. Tetrahedron Lett. 2007, 48, 5623–5625.
  2. "Studies toward the Total Synthesis of Nakiterpiosin: Construction of the CDE Ring System by a Transannular Diels–Alder Strategy" Ito, T.; Ito, M.; Arimoto, H.; Takamura, H.; Uemura, D. Tetrahedron Lett. 2007, 48, 5465–5469.

2006

  1. "Stereoselective Construction of the Octalin Unit of Symbioimine Using an Intramolecular Diels–Alder Reaction" Sakai, E.; Araki, K.; Takamura, H.; Uemura, D. Tetrahedron Lett. 2006, 47, 6343–6345.
  2. "Improved Synthesis of the A–G Ring Segment of Brevetoxin B" Kadota, I.; Nishii, H.; Ishioka, H.; Takamura, H.; Yamamoto, Y. J. Org. Chem. 2006, 71, 4183–4187.

2005

  1. "Total Synthesis of Brevetoxin B" Kadota, I.; Takamura, H.; Nishii, H.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9246–9250. [highlighted in Synfacts 2005, 276.]

2003

  1. "Convergent Total Syntheses of Gambierol and 16-epi-Gambierol and Their Biological Activities" Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Satake, M.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 11893–11899.
  2. "Total Synthesis of Gambierol" Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46–47.

2002

  1. "Concise Synthesis of Cyclic Ethers via the Palladium–Catalyzed Coupling of Ketene Acetal Triflates and Organozinc Reagents. Application to the Iterative Synthesis of Polycyclic Ethers" Kadota, I.; Takamura, H.; Sato, K.; Yamamoto, Y. J. Org. Chem. 2002, 67, 3494–3498.
  2. "Syntheses of the AB and EFGH Ring Segments of Gambierol" Kadota, I.; Kadowaki, C.; Park, C.-H.; Takamura, H.; Sato, K.; Chan, P. W. H.; Thorand, S.; Yamamoto, Y. Tetrahedron 2002, 58, 1799–1816.

2001

  1. "Synthetic Studies towards Gambierol. Part 2: Synthesis of the EFGH Ring Segment" Kadota, I.; Kadowaki, C.; Takamura, H.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6199–6202.
  2. "Concise Synthesis of Cyclic Ethers via the Palladium–Catalyzed Coupling of Ketene Acetal Triflates and a Zinc Homoenolate. Synthesis of the DE and GH Ring Segments of Gambierol" Kadota, I.; Takamura, H.; Sato, K.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 4729–4731.
  3. "Synthesis of the J Ring Segment of Gambieric Acid" Kadota, I.; Takamura, H.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 3649–3651.