Stereoselective Total Synthesis of AI-77-B, a Gastroprotective Substance From Bacillus Pumilus AI-77

Journal of the American Chemical Society

Volumn 111, Issue 4, 1989, Pages 1524-1525

  Hamada, Yasumasa ^a   Kawai, Akiyoshi ^a   Kohno, Yasushi ^a   Hara, Osamu ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 [[1 (3,4 DIHYDRO 8 HYDROXY 1 OXO 1H 2 BENZOPYRAN 3 YL) 3 METHYLBUTYL]AMINO] 4,5 DIHYDROXY 6 OXO 3 AMMONIOHEXANOATE;

DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRELIMINARY COMMUNICATION;

EID: 0024500342     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00186a071     Document Type: Article

References (10)

1. “New Methods and Reagents in Organic Synthesis. 83”. For Part 82, see: Kawai, A.; Hara, O.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1988, 29, 6331.
2. Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M.; Iitaka, Y. Tetrahedron Lett. 1982, 23, 5435. (b) Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M. Agric. Biol. Chem. 1982, 46, 1823. (c) Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M. Tetrahedron 1984, 40, 2519.
3. Structurally analogous compounds are known; see: (a) Okazaki, H.; Kishi, T.; Beppu, T.; Arima, K. J. Antibiot. 1975, 28, 717. (b) Ito, J.; Omoto, S.; Shomura, T.; Nishizawa, N.; Miyado, S.; Yuda, Y.; Shibata, U.; Inoue, S. J. Antibiot. 1981, 34, 611. (c) Ito, J.; Shomura, T.; Omoto, S.; Miyado, S.; Yuda, Y.; Shibata, U.; Inoue, S. Agric. Biol. Chem. 1982, 46, 1255. (d) Ito, J.; Omoto, S.; Nishizawa, N.; Kodama, Y.; Inoue, S. Agric. Biol. Chem. 1982, 46, 2659.
4. Shimojima, Y.; Hayashi, H. J. Med. Chem. 1983, 26, 1370.
5. Hauser, F. M.; Pogany, S. A. Synthesis 1980, 814.
6. Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1980, 30, 1921. (b) Hamada, Y.; Shibata, M.; Sugiura, T.; Kato, S.; Shioiri, T. J. Org. Chem. 1987, 52, 1252.
7. Thottathil, J. K.; Moniot, J. L.; Mueller, R. H.; Wong, M. K. Y.; Kissick, T. P. J. Org. Chem. 1986, 51, 3140.
8. Bieg, T.; Szeje, W. Synthesis 1987, 317.
9. Mizuno, A.; Hamada, Y.; Shioiri, T. Synthesis 1980, 1007.
10. Shioiri, T. J. Synth. Org. Chem. Jpn. 1979, 37, 856. (b) Takuma, S.; Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 3147.