Asymmetric synthesis of the C(1)-C(47) backbone of antitumour antibiotic A83586C

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9345-9348

  Hale, Karl J ^a   Cai, Jiaqiang ^a   Delisser, Vern M ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030599664     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82960-7     Document Type: Article

References (17)

1. 1. (a) A83586C: Smitka, T.A.; Deeter, J.B.; Hunt, A.H.; Mertz, F.P.; Ellis, R.M.; Boeck, L.D.; Yao, R.C., J. Antibiotics, 1988, 41, 726;
2. (b) Azinothricin: Maehr, H.; Liu, C.M.; Palleroni, N.J.; Smallheer, J.; Todaro, L.; Blount, J.F., J. Antibiotics, 1986, 39, 17;
3. (c) Citropeptin: Nakagawa, M.; Hayakawa, Y.; Furihata, K.; Seto, H., J. Antibiotics, 1990, 43, 477.
4. 2. Hale, K.J.; Delisser, V.M.; Yeh, L.-K.; Peak, S.A.; Manaviazar, S.; Bhatia, G.S., Tetrahedron Lett., 1994, 35, 7685.
5. 3. Hale, K.J.; Manaviazar, S.; Delisser, V.M., Tetrahedron, 1994, 50, 9181.
6. 4. Stelakatos, G.C.; Paganou, A.; Zervas, L., J. Chem. Soc. C, 1966, 1191.
7. 5. Durette, P.L.; Baker, F.; Barker, P.L.; Boger, J.; Bondy, S.S.; Hammond, M.L.; Lanza, T.J.; Pessolano, A.A.; Caldwell, C.G., Tetrahedron Lett., 1990, 31, 1237.
8. 6. Carpino, L.A.; Han, G.Y., J. Org. Chem., 1972, 34, 3404.
9. 7. Hale, K.J.; Cai, J., Tetrahedron Lett., 1996, 37, 4233.
10. 8. Bartlett, P.A.; Johnson, W.S., Tetrahedron Lett., 1970, 4459.
11. 9. Castro, B.; Dormoy, J.R.; Evin, G.; Selve, C., Tetrahedron Lett., 1975, 1219.
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13. 11. Gellman, S.H.; Adams, B.R.; Dado, G.P., J. Amer. Chem. Soc., 1990, 112, 460; Dado, G.P.; Gellman, S.H., J. Amer. Chem. Soc., 1993, 115, 4228; Gallo, E.A.; Gellman, S.H., J. Amer. Chem. Soc., 1993, 115, 9774.
14. 11. Gellman, S.H.; Adams, B.R.; Dado, G.P., J. Amer. Chem. Soc., 1990, 112, 460; Dado, G.P.; Gellman, S.H., J. Amer. Chem. Soc., 1993, 115, 4228; Gallo, E.A.; Gellman, S.H., J. Amer. Chem. Soc., 1993, 115, 9774.
15. 11. Gellman, S.H.; Adams, B.R.; Dado, G.P., J. Amer. Chem. Soc., 1990, 112, 460; Dado, G.P.; Gellman, S.H., J. Amer. Chem. Soc., 1993, 115, 4228; Gallo, E.A.; Gellman, S.H., J. Amer. Chem. Soc., 1993, 115, 9774.
16. 12. Gung, B.W.; Zhu, Z., J. Org. Chem., 1996, 61, 6482.
17. 3) at 25 °C δ 203.2, 176.4, 175.7, 173.2, 172.4, 172.2, 170.2, 169.7, 137.6, 136.8, 133.5, 129.3, 99.6, 82.1, 80.1, 78.5, 67.5, 59.0, 52.8, 52.7, 52.6, 51.7, 50.5, 48.4, 47.9, 46.9, 38.7, 32.5, 31.9, 31.0, 28.3, 27.3, 25.7, 24.1, 23.6, 21.6, 20.9, 20.0, 19.4, 18.7, 17.8, 17.7, 14.9, 13.6, 13.3, 12.1, 11.4, 7.7 ppm.