Synthesis Matsuo

Harada A, Kawamura M, Matsuo T et al (2006) Synthesis and characterization of head-tail type polycation block copolymer as non-viral gene vector. Bioconjug Chem 17 3-5... 

Zhong Y-W, Matsuo Y, Nakamura E (2006) Convergent synthesis of a polyfunctionalized fullerene by regioselective five-fold addition of a functionalized organocopper reagent to C60. Org. Lett. 8 1463-1466. 

T. Nakajima, S. Kasamatsu, Y. Matsuo, Synthesis and characterization of fluorinated carbon nanotubes, European Journal of Solid State Inorganic Chemestry, vol. 33, pp. 831-840,1996. 

Miyatake, K., Zhou, H., Matsuo, T., Uchida, H. and Watanabe, M. 2004. Proton conductive polyimide electrolytes containing trifluoromethyl groups Synthesis, properties, and DMFC performance. Macromolecules 37 4961 966. 

Matsuo, L Isomura, M. Walton, R. Ajisaka, K., A new strategy for the synthesis of the core trisaccharide of asparagine-hnked sugar chains. Tetrahedron Lett. 1996,37, 8795-8798. 

Kobayashi S, Manabe K, Ishitani H, Matsuo J (2002) Science of synthesis, Houben-Weyl methods of molecular transformation, vol 4. Thieme, Stuttgart... 

In Chapter 2, Matsuo and Nakamura describe the synthetic developments of a subgroup of bowl-shaped it-conjugated corannulenes and expand the topic to the discussion of the synthesis of a novel class of organic fluorophores derived from C60, hoop-shaped condensed aromatic compounds. They are made by selective removal of ten sp2 carbon centers out of conjugation from the north and south pole regions of C60. The resulting 40-jr-electron [lOjcyclophenacenes excised... 

A new total synthesis of BTX B (1) was accomplished by Matsuo and co-workers in 2004 via the conpling of 5 and 30 (Scheme 2.4), each ether ring of which was stereoselectively and efficiently constmcted on the basis of Sml2-induced intra-molecular Reformatsky-type reaction... 

Matsuo et al. 2004). Several kinds of double reactions at the left and right sides were efficiently used throughout the synthesis. Thus, the total synthesis of BTX-B (1) was efficiently achieved with high stereoselectivity in 59 steps as the longest linear sequence and in total 90 steps with an average of 93% yield for each step. 

Matsuo, G., Kawamura, K., Hori, N., Matsukura, H., and Nakata, T. 2004. Total synthesis of brevetoxin-B. Journal of the American Chemical Society 126, 14374-14376. 

Matsuo, G., Hinou, H., Koshino, H., Suenaga, T, and Nakata, T. 2000. Efficient convergent synthesis of a transfused 6-6-6-6-membered tetracyclic ether ring system. Tetrahedron Letters 41, 903-906. 

Matsuo I, Eujimoto H, Isomura M, Ajisaka K. Chemoenzymatic synthesis of Gal alpha l-3Gal, Gal alpha l-3Gal beta... 

Matsuo et al. (57) also have prepared this peptide via solid-phase peptide synthesis. The protected decapeptide resin ester (V -Boc-Gln-His-Trp-Ser(OBzl)-Tyr(OBzl)-Gly-Leu-Arg (N02)-Pro-Gly-resin ester) that corresponds to the amino acid sequence of LH-RH/FSH-RH was synthesized using V -Boc chemistry by the method described by Stewart and Young (38), which starts with V -Boc-Gly-resin ester (1.0 g 0.35 mmole). The side-chain protections were as follows Ser and Tyr were protected by Bn groups. Gin by a Np group, Arg by a... 

Matsuo H, Arimura A, Nair RMG, Schally AV. Synthesis of 78. the porcine LH- and FSH-releasing hormone by the solid-phase method. Biochem. Biophys. Res. Commun. 1971 45 822-827. 

Kawamura, K., Hinou, H., Matsuo, G., Nakata, T. Efficient strategy for convergent synthesis of trans-fused polycyclic ethers based on an intramolecular Sml2-promoted cyclization of iodo ester. Tetrahedron Lett. 2003, 44, 5259-5261. 

Kobayashi, S., Manabe, K., Ishitani, H., Matsuo, J. I. Product subclass 16 silyl enol ethers. Science of Synthesis 2002,4, 317-369. 

I. Matsuo, K. Totani, A. Tatami, and Y. Ito, Comprehensive synthesis of ER related high-mannose-type sugar chains by convergent strategy, Tetrahedron, 62 (2006) 8262-8277. 

Minami, T., Nakayama. M.. Fujimoto, K., and Matsuo, S., A new approach to cyclopentane annulated compounds via l-(cyclopent-l-enylcarbonyl)vinylphosphonates, and synthesis and synthetic application of a-diethoxyphosphoryl-A Kbutenolides, Phosphorus, Sulfur Silicon Relat. Elem., 75,135,1993. 

Tsuji, K., Nakamura, K., Konishi, N., Tojo, T., Ochi. T.. Senoh, H.. and Matsuo, M., Studies on antiinflammatory agents. Part 4. Synthesis and pharmacological properties of 1,5-diarylpyrazoles and related derivatives, Chem. Pharm. Bull., 45. 987, 1997. 

Application to the synthesis of insect attractant Kiyooka S, Kaneko Y, Harada Y, Matsuo... 

J. Horii, H. Fukase, T. Matsuo, Y. Kameda, N. Asano, and K. Matsui, Synthesis and a-D-glucosidase inhibitory activity of substituted valiolamine derivatives as potential oral antidiabetic agents, J. Med. Chem., 29 (1986) 1038-1046. 

Matsuo and co-workers have described two syntheses of cerpegin (118) (231-233). In the first synthesis, reaction of the lithium salt of phenyl-thioacetonitrile (352) with treated with 2-methoxycarbonyl-5,5-dimethyl-2-buten-4-olide (353) at -78°C and then warmed to room temperature and treated with acid afforded a stereoisomeric mixture of 354 in 93% yield. Oxidation of 354 with mefa-chloroperbenzoic acid followed by reflux in benzene gave 355. Catalytic reduction (Pd-C-HCl) and treatment with base gave 356 in 44% yield. Various methylation procedures were unsuccessful, but reaction with methyl 4-toluene sulfonate in the presence of NaH gave 118 in 81% yield (Scheme 41) (231,232). 

The second Matsuo synthesis (233) was initiated with methyl 3-(2,2-dimethoxyethyl)-4-methyl-4-pentenoate (357) prepared (234) from carvone (239). Hydrolysis with lithium hydroxide followed by iodolactonization (I2-KI-NaHC03) and reduction with tri-n-butyl tin hydride in the presence of azobisisobutyronitrile in benzene under reflux afforded 358. The carbo-methoxy group was introduced with methyl chloroformate and LDA in quantitative yield, and reductive animation of 359 with methylamine and sodium cyanoborohydride gave the lactone 360. Heating of 360 with 10% Pd/C in decalin gave cerpegin (118) in 81% yield (Scheme 42) (233). 

Synthesis by hydrolysis of Mg3N2 and MgCl2. Large discrepancy with the data of Satake and Matsuo (1984). 

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