A practical and efficient synthesis of (±)- camptothecin

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6745-6748

  Chavan, Subhash P ^a   Venkatraman, M S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Camptothecin; DIBAL H reduction; Glycine; Intramolecular Michael reaction; Wittig reaction

Indexed keywords

ALKENE; AMIDE; CAMPTOTHECIN; DIPYRONE; GLYCINE; IRINOTECAN; QUINOLINE; TOPOTECAN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REDUCTION; SYNTHESIS;

EID: 0032505228     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01415-4     Document Type: Article

References (21)

1. [1] Wall ME, Wani MC, Cook CE, Palmer KH, McPhail AT, Sim GA. J. Am. Chem. Soc. 1966; 88: 3888-3890.
2. [2] Kingsbury WD, Boehm JC, Jakas DR, Holden KG, Hecht SM, Gallagher G, Caranfa MJ, McCabe FL, Faucette LF, Johnson RK, Hertzberg RP. J. Med. Chem. 1991; 34: 98-107.
3. [3] Hutchinson CR. Tetrahedron 1981; 37: 1047-1065.
4. [4] Suffness M, Cordell GA. Antitumour Alkaloids In Brossi A, editor The Alkaloids Vol 25. Orlando Florida, Academic press, 1985: 73-89.
5. [5] Curran DP, Liu H. J. Am. Chem. Soc. 1992; 114: 5863-5864.
6. [6] Rama Rao AV, Yadav JS, Valluri M. Tetrahedron Lett. 1994; 35: 3613-3616.
7. [7] Comins DL., Baevsky MF, Hong H. J. Am. Chem. Soc. 1992; 114: 10971-10972.
8. [8] Jew S-S, Ok KD, Kim H-J, Kim MG, Kim JM, Geong MH, Cho Y-S. Tetrahedron Asymm. 1995; 6: 1248-1248.
9. [9] Ciufolini MA, Roschangar F. Angew. Chem. Int. Ed. Engl. 1996; 35: 1692-1694.
10. [10] O'Donnell MJ, Polt RL. J. Org. Chem. 1982; 47: 2663-2666.
11. [11] Joucla M, El Goumizli M, Fouchet B. Tetrahedron Lett. 1986; 27: 1677-1680.
12. [12] Hayashi T, Kanehira K, Hagihara T, Kumada M. J. Org. Chem. 1988; 53: 113-120.
13. [13] Tang C, Rapoport H. J. Am. Chem. Soc. 1972; 94: 8615-8616.
14. [14] Pappo R, Allen DS(Jr.), Lemieux RU, Johnson WS. J. Org. Chem. 1956; 21: 478-479.
15. [15] Kuchar M, Kakac B, Nemecek O, Kraus E, Holubek J. Collect. Czech., Chem. Comm. 1973; 38: 447-454.
16. [16] Olah GA, Narang SC, Balaram Gupta BG, Malhotra R. J Org. Chem. 1979; 44: 1247-1251.
17. [17] Massiot G, Mulamba T. J. Chem. Soc., Chem. Commun. 1984; 715-716.
18. [18] Kametani T, Ohsawa T, Ihara M. J. Chem. Soc., Perkin Trans. 1 1981; 1563-1568.
19. [19] Kraiss G, Povarny T, Scheiber P, Nador K. Tetrahedron Lett. 1973; 2359-2360.
20. [20] Shen W, Coburn CA, Bommann WG, Danishefsky SJ. J. Org. Chem. 1993; 58: 611-617.
21. 13CMR). All new compounds gave satisfactory elemental analysis.