Total syntheses of O4,9-dimethyl stealthins A and C

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3973-3976

  Koyama, Hiroya ^a   Kamikawa, Tadao ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 O,9 O DIMETHYLSTEALTHIN A; 4 O,9 O DIMETHYLSTEALTHIN C; FLUORENONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

LATEOLABRAX JAPONICUS; LETHRINIDAE; STREPTOMYCES VIRIDOCHROMOGENES;

EID: 0030914749     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00793-4     Document Type: Article

References (10)

1. Shin-ya, K.; Furihata, K.; Teshima, Y.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 1992, 33, 7025-7028.
2. Gould, S.J.; Chen, J.; Cone, M.C.; Gore, M.P.; Melville, C.R.; Tamaya, N. J. Org. Chem. 1996, 61, 5720-5721.
3. Gould, S.J.; Melville, C.R.; Cone, M.C.; Chen, J.; Carney, J.R. J. Org. Chem. 1997, 62, 320-324.
4. Grunwell, J.R.; Heinzman, S.W. Tetrahedron Lett. 1980, 21, 4305-4308.
5. Hass, H.B.; Bender, J.D. Organic Syntheses Coll. Vol. 4, Wiley: New York, 1963; pp. 932-934.
6. Comins, D.L.; Brown, J.D. J. Org. Chem. 1984, 49, 1078-1083.
7. Iihama, T.; Fu, J.-m.; Bourguignon, M.; Snieckus, V. Synthesis, 1989, 184-187.
8. -1. From the structure of 12 this band is not explicable, so it may be a mistake.
9. 3) δ 21.5, 55.9, 56.4, 111.1, 114.7, 114.8, 117.3, 118.1, 120.0, 121.2, 131.0, 133.6, 136.5, 138.1, 140.6, 142.5, 150.1, 51.5, 161.0, 180.3. Among the three tautomers assumed, the one corresponding to the natural product was shown to be the most stable by means of MOPAC calculation.
10. 3) δ 21.0, 56.1, 56.7, 66.4, 110.2, 114.6, 114.9, 117.6, 118.2, 121.2, 122.6, 131.5, 134.0, 135.7, 136.3, 139.8, 142.5, 151.7, 151.8, 161.2, 170.8, 180.7.