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Shiina Lab
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This lab carries out total synthesis of natural organic molecules and bioactive compounds with the desired three-dimensional structures.
AboutAbout the lab
Synthesizing organic molecules with the desired stereostructure.
The Shiina Lab develops total synthesis methods that produce natural organic molecules and bioactive compounds, such as antibacterial and anticancer agents, with the desired three-dimensional structure.
Bioactive compounds such as pharmaceuticals, agrochemicals, and fragrances have multiple asymmetric carbons, and in most cases only one stereoisomer is effective.
The lab also develops new reagents for dehydration condensation reactions that form esters and amides, and MNBA is one of them.
Prof. Shiina also serves as Director of the Drug Discovery Research and Development Center, Research Institute for Science and Technology, Tokyo University of Science.
Key terms
- Total synthesis
- Artificially building a complex, naturally occurring compound from simple starting materials through a series of chemical reactions
- Asymmetric carbon
- A carbon atom bonded to four different partners. It gives rise to stereoisomers with different three-dimensional structures
- Dehydration condensation reaction
- A reaction in which two molecules join with the loss of water. It is used to form ester and amide bonds
- MNBA
- Abbreviation of 2-methyl-6-nitrobenzoic anhydride. A condensing agent that achieved an extremely fast lactone-forming reaction
NewsLab news
An award-winning paper from the Shiina Lab was published in the Journal of Synthetic Organic Chemistry, Japan
A paper from a joint study with the National Cancer Center was published in JBC
Succeeded in the total synthesis of merrilianin, a plant-derived natural compound
Published a paper on the asymmetric total synthesis of merrilianin in Organic Letters
ResearchResearch themes
Organic synthesis techniques have advanced, but substances that cannot be made efficiently and methods for making only the desired three-dimensional structure remain challenges. The lab's main theme is developing stereoselective total synthesis methods for natural organic molecules such as terpenes and macrolides, and for bioactive compounds such as antibacterial, anticancer, and immunosuppressive agents.
*Illustrative imageAsymmetric synthesis of natural pharmacologically active compounds
Using original methods such as stereoselective synthesis of optically active polyoxy compounds and efficient lactone formation, the lab has established synthetic routes to pharmacologically active natural compounds. It continues synthetic studies of compounds such as botcinin and merrilianin.
*Illustrative imageStereocontrol of compounds with many hydroxyl groups
The lab synthesizes compounds with multiple hydroxyl groups in the molecule while controlling the stereochemistry of the asymmetric carbons attached to them. Using the asymmetric Mukaiyama aldol reaction and kinetic optical resolution, it develops methods for building the basic skeletons of natural organic compounds.
*Illustrative imageEfficient synthesis of hormonal anticancer agents
The lab developed a three-component coupling method that carries out allylation and alkylation of aromatic aldehydes in sequence, and found that tamoxifen, a breast cancer drug, can be obtained in a few steps. It is now preparing analogs and investigating their pharmacological activity.
*Illustrative imageEster and amide bond formation under mild conditions
The lab develops new reagents for dehydration condensation reactions that form esters and amides, including MNBA and the peptide synthesis reagent CDOP. It is using these reagents to study the synthesis of eushearilide and tetrahydrolipstatin.
MembersFaculty
The Shiina Lab's members consist of faculty, project researchers, administrative staff, and doctoral, master's, and undergraduate students.As of 2026
- ProfessorIsamu Shiina
- LecturerTakashi Murata
- Assistant ProfessorRyosuke Koyama
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Report an errorAbout the images
The top and research theme images are illustrative and were not taken at the lab. They are cropped from Wikimedia Commons images. Cropped CC BY-SA images are provided under the same CC BY-SA license as the original (version shown on each line).
- Top image: “Organic Chemistry Lab 5 by marthou” Marthou / CC BY-SA 4.0 (cropped)
- Asymmetric synthesis of natural pharmacologically active compounds: “Hibiscus medicinal plant” Prathvi Acharya / CC BY-SA 4.0 (cropped)
- Stereocontrol of compounds with many hydroxyl groups: “Granulated White Sugar with Large Crystals, Bright Side Light” Tobias Erbsland / CC BY-SA 4.0 (cropped)
- Efficient synthesis of hormonal anticancer agents: “Drug synthesis” Linda Bartlett (Photographer) / Public domain (cropped)
- Ester and amide bond formation under mild conditions: “Separatory funnel” 作者不詳 / Public domain (cropped)
- Related lab (松田研究室): “Palladium catalyst solutions with varying concentration” / CC BY-SA 4.0 (cropped)
- Related lab (川﨑研究室): “Discoveries from Asteroid Bennu- Media Briefing Graphics (SVS14772 - NASA Chiral Molecules V2)” NASA's Scientific Visualization Studio - NASA/Nicola Fox, Smithsonian Institution/Timothy McCoy, Natural History Museum, London/Sara Russell, NASA/GSFC/Daniel Glavin, NASA/GSFC/Jason Dworkin, NASA/GSFC/Rani Gran, eMITS/Dan Gallagher, Jacobs-JETS/Scott Eckley, Barrios Technology Ltd/Rachel Barry, ADNET Systems, Inc./Lonnie Shekhtman / Public domain (cropped)
- Related lab (石川研究室): “Scanning electron microscope view of iron crystal (S72-55208)” NASA Johnson Space Center / Public domain (cropped)
- Related lab (貞清研究室): “Potassium trisoxalatoiron(III) trihydrate in vial” EryZ / CC BY-SA 3.0 (cropped)
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