Total synthesis of (±)-phosphonothrixin

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6621-6624

  Fields, Stephen C ^a  

^a DOW AGROSCIENCES LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; KETONE DERIVATIVE; NATURAL PRODUCT; PHOSPHONOTHRIXIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG ISOLATION; DRUG SYNTHESIS; OXIDATION;

EID: 0032505194     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01403-8     Document Type: Article

References (14)

1. 1. Hidaka, T.; Hidaka, M.; Seto, H. J. Antibiotics, 1992, 45, 1977 and the references cited therein.
2. 2. Kondo, Y.; Shomura, T.; Ogawa, Y.; Tsuruoka, T.; Watanabe, H.; Totsukawa, K.; Susuki, T.; Moriyama, C.; Yoshida, J.; Inouye, S.; Niida, T. Sci. Reports of Meiji Seika Kaisha, 1973, 13, 34.
3. 3. Bayer, E.; Gugel, K.; Hagele, K.; Hagenmaier, H.; Jessipow, S.; Konig, W.; Zahner, H. Helv. Chim. Acta., 1972, 55, 224.
4. 4. Omura, S.; Murata, M.; Hanaki, H.; Hinotozawa, K.; Oiwa, R.; Tanaka, H. J. Antibiotics, 1984, 37, 829.
5. 5. Takahashi, E.; Kimura, T.; Nakamura, K. Jpn. Kokai Tokkyo Koho, 10 pp. JP 07008282 A2 950113 Heisei.
6. 6. Takahashi, E; Kimura, K.; Nakamura, K.; Arahira, M.; Iida, M. J. Antibiotics, 1995, 48, 1124.
7. 7. Kimura, K.; Nakamura, K.; Takahashi, E; J. Antibiotics, 1995, 48, 1130.
8. 8. Nakamura, K.; Kimura, K.; Kanno, H.; Takahashi, E; J. Antibiotics, 1995, 48, 1134.
9. 9. Nakamura, K. and Yamamura, S. Tetrahedron Lett., 1997, 38, 437.
10. 2+ and I ntramolecular displacement with tethered dialkyl or trialkyl phosphites all failed in our hands.
11. 11. Approximately $2 per gram from Aldrich.
12. 12. For a review: Basavaiah, D.; Rao, P.; Hyma, R. Tetrahedron, 1996, 52, 8001.
13. 13. Janecki, T. and Bodalski, R. Synthesis, 1990, 799.
14. 14. The major E-isomer was purified away from the < 5% minor Z-isomer by column chromatography.