Synthesis Sasaki

Hydrogenation of carbon dioxide in the presence of an epoxide generates a mixture of the diol, its formate esters, and the cyclic carbonate. While the reaction has been shown to operate in high yield (1300 TON for the cyclic carbonate Eq. (10)) [93], the fact that a mixture is generated and that the cyclic carbonate could be made more cleanly in the absence of H2 makes the reaction uninteresting for synthesis. Sasaki s group showed that this reaction in the presence of an amine base gives CO rather than cyclic carbonate (Eq. (11)) [94]. The epoxide then serves as a trap for the water. 

Kurihara, K., Sasaki, K., Kawarada, M., and Koshino, M., High Rate Synthesis of Diamond by DC Plasma Jet Chemical Vapor Deposition, Phys. Lett., 52(6) 437 38 (1988)... 

Sasaki M (2006) Recent Advances in Total Synthesis of Marine Polycyclic Ethers. 5 149-178 Satake M (2006) Marine Polyether Compounds. 5 21-51 Shan R, see Maiti SN (2006) 2 207-246... 

The remaining four chapters of the present volume involve topics new to the series. Two of them deal with specific groups of compounds (C. J. Moody on Azodicarbonyl Compounds and T. Sasaki on Heteroada-mantanes ) and two others deal with the Use of Transition Organome-tallic Compounds in Heterocyclic Synthesis (J. L. Davidson and P. N. Preston) and Sulfur Transfer Reagents (M. Davis). 

S. Kojima, T. Hasegawa, T. Yonemura, K. Sasaki, K. Yamamoto, Y. Makimura, T. Takahashi, T. Suzuki, Y. Susuki, and K. Kobayashi, Ruthenium complexes carrying a disialo complex-type oligosaccharide Enzymatic synthesis and its application to a luminescent probe to detect influenza viruses, Chem. Commun. (2003) 1250-1251. 

For general application of these chiral ligands, see (a) Kagan, H. B. Chiral Ligands for Asymmetric Catalysis in Morrison, J. D. ed. Asymmetric Synthesis, vol. 5, Chap. 1, Academic Press, New York, 1985. (b) Kagan, H. B., Sasaki, M. Optically Active Phosphines Preparation, Uses and Chiroptical Properties in Hartley, F. R. ed. The Chemistry of Organo Phosphorous Compounds, John Wiley Sons, New York, 1990, vol. 1, Chap. 3. 

Y Sohma, M Sasaki, Y Hayashi, T Kimura, Y Kiso. Novel and efficient synthesis of difficult sequence-containing peptides through O-N intramolecular acyl migration reaction of O-acyl isopeptides. Chem Commun 124, 2004. 

Oh S, Kim BJ, Singh NP, Lai H, Sasaki T. (2009) Synthesis and anti-cancer activity of covalent conjugates of artemisinin and a transferring-receptor targeting peptide. Cancer Lett 274 33-39. 

Oikawa M, Ikoma M, Sasaki M (2005) Parallel synthesis of tandem Ugi/Diels-Alder reaction products on a soluble polymer support directed toward split-pool realization of a small molecule library. Tetrahedron Lett 46 415-418... 

M. Nomura, S. Shuto, M. Tanaka, T. Sasaki, S. Mori, S. Shigeta, and A. Matsuda, Nucleosides and Nucleotides. 185. Synthesis and biological activities of 4 -a-C-branched-chain sugar pyrimidine nucleosides, J. Med. Chem., 42 (1999) 2901-2908. 

F. Yamamoto, S. Sasaki, M. Maeda, Positron labeled antioxidants Synthesis and tissue biodistribution of 6-deoxy-6-[ F]fluoro-L-ascorbic acid, Appl. Radiat. Isot. 43 (1992) 633-639. 

Y. Sasaki, A. Niida, T. Tsuji, A. Shigenaga, N. Fujii, A. Otaka, Stereoselective synthesis of (Z)-alkene-containing proline dipeptide mimetics, J. Org. Chem. 71 (2006) 4969 979. 

Japanese workers prepared examples of 2-alkenyl-4,5-oxazolediones 40a and 40b, which are key intermediates in the synthesis of alkenoyl isocyanates 41a and 41b (Scheme 6.13). These reactive monomers are precursors to a variety of functionalized polymers including instantaneously curable compositions. Thus, reaction of oxalyl chloride with acrylamide 39a or methacrylamide 39b affords 40a and 40b isolated as hydrochloride salts in high yields. Subsequent decomposition of the 2-alkenyl-4,5-oxazolediones in the presence of a metal halide or synthetic zeolite affords 41a and 41b contaminated with varying amounts of 42a and 42b. The synthesis and reactions of other 2-substituted 4,5-oxazolediones have been described independently by Speziale and co-workers ° and Sasaki and co-workers. ... 

However, these have not been the only approaches to the synthesis of these ring systems. For example, Sasaki et al. were able to use an intramolecular nucleophilic ring opening of an epoxide with sodium dimsylate to form the oxepane ring as illustrated in the conversion of 34 to 35 <99JOC9399>. 

Olah Nojima Kerekes Synthesis 1973, 487. For other methods of preparing acyl fluorides, see Mukaiyama Tanaka Chem. Lett. 1976, 303 Ishikawa Sasaki Chem. Lett. 1976, 1407,... 

Sec, for example, Jardinc McQuillin Chem. Commun. 1970,626 Hanaya Muramatsu Kudo Chow J. Chem. Soc., Perkin Trans. 11979,2409 Ono Sasaki Yaginuma Chem. Ind. (London) 1983,480 Osby Ganem Tetrahedron Lett. 1985, 26. 6413 Pctrini Ballini Rosini Synthesis 1987, 713 He Zhao Pan Wang Synth. Commun. 1989, 19, 3047. 

An impressively complex natural molecule is maitotoxin, a remarkable biologically active compound produced by the dinoflagellate Gambierdiscus toxicus. Presently, the total synthesis of this natural substance seems to be beyond the possibilities offered by modem synthesis. M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. Int. Ed. 1996, 35, 1672-1674. 

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