Synthetic study on ecteinascidin 743 starting from D-glucose

Synlett

Volumn , Issue 7, 1999, Pages 1103-1105

  Endo, Atsushi ^a   Kann, Toshiyuki ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Bicyclo 3.3.1 system; D glucose; Ecteinascidin 743; Imine

Indexed keywords

ALDEHYDE; BROMIDE; COPPER; EPOXIDE; GLUCOSE; IMINE; NITROGEN; PHENOL; SULFONAMIDE; TRABECTEDIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOSPECIFICITY;

EID: 0032769747     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3161     Document Type: Article

References (14)

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6. Intramolecular ortho-addition of a phenol to an aldehyde succeeded in the following simple model.
7. For previous work on the synthesis of the saframycins: (a) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957.
8. (b) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712.
9. (c) Saito, N.; Yamauchi, R.; Nishioka, H.; Ida, S.; Kubo, A. J. Org. Chem. 1989, 54, 5391.
10. Epoxide 5 was prepared from D-glucose in five steps through a known procedure: Methods in Carbohydrate Chemistry, Vol. II 190, Academic Press, New York 1963.
11. Martin, O. R.; Kurz, K. G.; Rao, S. P. J. Org. Chem. 1987, 52, 2922.
12. A similar difference of reactivity in the methyl D-glucofuranoside derivatives has been reported: Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971.
13. A similar Pictet-Spengler cyclization via an acyliminium was performed in the total synthesis of the saframycins; ref 7b. Cyclization proceeded exclusively to give the desired product.
14. 2, (56%).