Tokyo Institute of Technology · Medicine
Professor Tadashi Eguchi's research lab specializes in the total synthesis of complex natural products, with a focus on structurally unique and biologically significant lipids and antibiotics. The lab develops innovative synthetic strategies—particularly involving stereoselective coupling methods like McMurry coupling and Julia coupling—for constructing macrocyclic and polycyclic architectures found in archaeal membrane lipids and macrolide antibiotics. A key emphasis is placed on enabling access to chemically defined, stereochemically homogeneous natural products and their analogs for structure-activity and physicochemical studies. The lab also integrates biosynthetic gene cluster analysis with synthetic chemistry to unravel the enzymatic origins of complex natural product scaffolds.
Figures are computed from collected data and may differ slightly.
Total synthesis of archaeal 36-membered macrocyclic diether lipid 2 is reported. The synthesis is based upon stereoselective preparation of functionalized isoprenoid chains, ether-linkage formation between the isoprenoid chains with a glycerol derivative, and the ultimate intramolecular dicarbonyl coupling using low-valent titanium known as McMurry coupling. This synthetic method has successfully provided the first practical route to chemically defined archaeal macrocyclic membrane lipids, which
Total synthesis of archaeal 72-membered macrocyclic tetraether lipids 3a and 3b is reported. The synthesis was principally composed of preparation of the functionalized half-sized diether compounds 11 and 15 first followed by appropriate dimerization through Julia coupling and final macrocyclization of the crucial dialdehydes 23 and 31 by McMurry coupling. This strategy appeared to be advantageous for the stereoselective synthesis of both natural 72-membered tetraether lipids 3a and 3b using com
Cremimycin is a 19-membered macrolactam glycoside antibiotic based on three distinctive substructures: 1) a β-amino fatty acid starter moiety, 2) a bicyclic macrolactam ring, and 3) a cymarose unit. To elucidate the biosynthetic machineries responsible for these three structures, the cremimycin biosynthetic gene cluster was identified. The cmi gene cluster consists of 33 open reading frames encoding eight polyketide synthases, six deoxysugar biosynthetic enzymes, and a characteristic group of fi
The absolute stereochemistry of FD-594 1, a new cytotoxic antibiotic, was determined by X-ray diffraction, and its conformation was studied by CD and NMR spectroscopy. The aglycon part of 1 was found to have (3R,6S,7S) configuration. Particularly interesting was the solvent-dependent atropisomerism of 1 and related compounds. The CD spectra of 1 exhibited in two solvent systems almost opposite mirror-image curves depending on the solvent. While a large negative Cotton effect (Δε = −33.9, 279 nm)
Open papers in the app to read, cite, and organize with AI.
