A5072226949- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Synthetic Organic Chemistry Methods
- Marine Sponges and Natural Products
- Asymmetric Synthesis and Catalysis
- Chemical synthesis and alkaloids
- Crystallography and molecular interactions
- Advanced Synthetic Organic Chemistry
- Traditional and Medicinal Uses of Annonaceae
- Microbial Natural Products and Biosynthesis
- Oxidative Organic Chemistry Reactions
- Synthesis and Catalytic Reactions
- Carbohydrate Chemistry and Synthesis
- Marine Toxins and Detection Methods
- Synthesis of heterocyclic compounds
- Fusion materials and technologies
- Plant biochemistry and biosynthesis
- Synthesis of Organic Compounds
- Histone Deacetylase Inhibitors Research
- Synthesis and Biological Evaluation
- Microstructure and mechanical properties
- Phytochemistry and Bioactivity Studies
- Vanadium and Halogenation Chemistry
- Thermodynamic and Structural Properties of Metals and Alloys
- Gyrotron and Vacuum Electronics Research
Japan Women's University
2017-2025
RIKEN Center for Sustainable Resource Science
2019
Tokyo University of Pharmacy and Life Sciences
2003-2018
The University of Tokyo
1993-2017
Tohoku University
1995-2016
Tohoku Medical and Pharmaceutical University
2008-2011
Komatsu (Japan)
2009
Nihon Pharmaceutical University
2007
University of Missouri
2005
Hokkaido University
2004
Fasicularin is a structurally novel thiocyanate-containing alkaloid isolated from the ascidian Nephteis fasicularis. Early biological experiments suggested that this compound's cytotoxic properties may stem its ability to damage cellular DNA. Sequence gel analysis reveals treatment of 5'-32P-labeled DNA duplex with fasicularin in pH 7.0 buffer causes strand cleavage selectively at guanine residues. Further indicate production these base-labile lesions involves alkylation residues by...
The first total synthesis of tricyclic marine alkaloids (±)-fasicularin (2) and (±)-lepadiformine (5) was accomplished. key common strategic element for the is stereocontrolled intramolecular hetero-Diels−Alder reaction an N-acylnitroso moiety to exocyclic diene with or without bromine substitution control syn-facial anti-facial selectivity, respectively, leading trans- cis-fused decahydroquinoline ring systems 21 39 involving simultaneous introduction nitrogenated quaternary center in a...
A very short and efficient enantioselective total synthesis of the tricyclic marine alkaloids (−)-lepadiformine (3), (+)-cylindricine C (1c), (−)-fasicularin (4) has been developed utilizing formyloxy 1-azaspiro[4.5]decane 5 as a common intermediate. The key strategic element for was formic acid-induced intramolecular conjugate azaspirocyclization, which proved to be highly stereoselective way rapid construction 1-azaspirocyclic substructure these natural products in single operation. Thus,...
An azaphilone, 6,7-iso-felinone A (2), was isolated from Diaporthales sp. KT3922 along with the known felinone (1). While compound 2 exhibited weak Cotton effects, its naphthoate derivative (2a) displayed pronounced enabling determination of absolute configuration through electronic circular dichroism (ECD) spectral analysis. Interestingly, spectroscopically derived relative structure proved identical to previously reported hypoillexidiol (3) and xylariphilone (4). However, substantial...
Mitochondria play a central role in cellular energy metabolism and homeostasis, their dysfunction is closely linked to the progression of age-related diseases. The mitochondrial ubiquitin ligase MITOL (also known as MARCHF5) key regulator dynamics function, reduced expression mouse heart has been implicated cardiac aging. In this study, we identified berberrubine compound that promotes activates mitochondria. We further assembled group berberrubine-based compounds, including its quinoid form...
A short synthesis: The naturally occurring (−)-lepadiformine ((−)-3) was prepared in nine steps 31.4 % overall yield. key step involved the formation of 2 by spirocyclization N-acyliminium ion generated from 1. Furthermore, HPLC analysis synthetic material and natural product established absolute configuration 3 as 3S,5R,7aS,11aS. Bn=benzyl, Boc=tert-butoxycarbonyl.
Abstract The first total synthesis of tricyclic marine alkaloids (±)-fasicularin (2) and (±)-lepadiformine (5) has been accomplished. key common strategic element for the is stereocontrolled intramolecular hetero-Diels–Alder reaction an N-acylnitroso moiety with exocyclic diene or without bromine substitution to control syn-facial anti-facial selectivity, respectively. This leads trans- cis-fused decahydroquinoline ring systems 13 23 involving simultaneous introduction nitrogenated...
A concise total synthesis of spirocurcasone was accomplished. Key features the involved a vinylogous Mukaiyama aldol reaction, Carroll rearrangement β-keto allyl ester derivative, an intramolecular condensation, and spiro ring formation by ring-closing metathesis pentaene compound. This synthetic work complete in nine steps from (S)- or (R)-perillaldehyde without use protecting groups. Interestingly, optical rotation different reported value natural product.
The first total synthesis of (±)-naupliolide has been achieved. synthetic method includes a Simmons-Smith cyclopropanation an allyl alcohol, diastereoselective cleavage benzylidene acetal group, radical cyclization aldehyde with cyclopropane ring, and construction eight-membered ring by ring-closing metathesis.
A novel chiral 1,3-diketone possessing C2 symmetry was synthesized and utilized in the asymmetric synthesis of guignardone H I by employing sequential condensation–6π-electrocyclization reactions with followed stereoselective hydrogenation as key steps. Although synthetic compounds differed from natural I, we realized that C4-epimers proposed structures for were actual structures.
The thymus contains many apoptotic cells that arise from the process of positive and negative selection. Both thymic macrophages nurse cells/nursing epithelial (nursing TECs), non-professional phagocytes, recognize ingest without inflammation or tissue damage. Previously we reported human scavenger receptor class B (SR-B1) is involved in recognition thymocytes by nursing TECs. In this study, examined expression role a phosphatidylserine (PSR). This believed to participate clearance cells....
We efficiently synthesized (+)-sesquicillin (a glucocorticoid antagonist) and (-)-nalanthalide potassium channel Kv1.3 blocker) in a convergent unified manner starting from (+)-5-methyl-Wieland-Miescher ketone.The synthesis involved the following key steps: (i) [2,3]-Wittig rearrangement of stannylmethyl ether to install stereogenic center at C9 exo-methylene functionality C8 present trans-decalin portion, (ii) coupling reaction portion with -pyrone moiety assemble requisite whole carbon...
The first total synthesis of albaflavenone, a novel antibiotic sesquiterpene, has been accomplished via the concise construction its zizaene skeleton utilizing sequential intramolecular aldol condensation followed by chemo- and diastereoselective reduction conjugated carbon-carbon double bond. This synthetic work was completed in nine steps from 2-cyclopenten-1-one as starting material without use protecting groups with high stereocontrol. In addition, absolute configuration naturally...
The first asymmetric total synthesis of pleurospiroketals A and B has been accomplished in 16 steps from 5-methyl-5-hexenoic acid. Key features the are highly syn-selective Evans aldol reaction, ring-closing metathesis, diastereoselective dihydroxylation acid-mediated spiroketalization.
Abstract The tricyclo[5.3.1.04,11]undecane framework of presilphiperfolan-8-ol, tricyclic sesquiterpene alcohol was constructed by intramolecular aldol condensation and the McMurry coupling from two types diketone compounds, which were obtained (+)-pulegone through a five-step process. This synthetic route does not require use any protective groups.
The first total synthesis of tricyclic sesquiterpene (±)‐toxicodenane A has been accomplished. This synthetic work was completed in 12 steps from dimedone through diastereoselective reductive desymmetrization 2,2‐disubstituted 5,5‐dimethylcyclohexane‐1,3‐dione, stereocontrolled allylation, ring‐closing metathesis a diene compound to yield bicyclic compounds that bear seven‐membered ring, and construction the oxygen‐bridged moiety neighboring group assisted ring‐opening reaction an epoxide as...
The first total synthesis of tricyclic bisnorsesquiterpene paralemnolide A, isolated from the soft coral Paralemnalia thyrsoides, was achieved. This features lactonization cyclohexene derivative having a tert-butyl ester via stereoselective epoxidation followed by treatment with Brønsted acid and construction novel skeleton an intramolecular Reformatsky–Honda reaction.
Total synthesis of the proposed structure a polyketide isolated from Phialomyces macrosporus is described. The involved chemoselective epoxidation, regioselective epoxide ring opening, chemo- and diastereoselective dihydroxylation, vinylation lactone accompanied by formation furan ring.
The first enantioselective total synthesis of eremophilane-type sesquiterpenoids, sagittacin E and related natural products, was achieved.