A formal total synthesis of (-)-cephalotaxine

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 7, 1999, Pages 983-987

  Ikeda, Masazumi ^a   Serry, A A ^a   Bialy, El ^a   Hirose, Ken Ichi ^a   Kotake, Miho ^a   Sato, Tatsunori ^a   Bayomi, Said M M ^b   Shehata, Ihsan A ^b   Abdelal, Ali M ^b   Gad, Laila M ^b   Yakura, Takayuki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b Mansoura University 35516   (Egypt)

Author keywords

( ) cephalotaxine; D proline; Friedel Crafts alkylation; Intramolecular aldol condensation; Intramolecular Heck reaction; Pummerer reaction

Indexed keywords

CEPHALOTAXINE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; STRUCTURE ANALYSIS;

EID: 0344436043     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.983     Document Type: Article

References (23)

1. For reviews of the Cephalotaxus alkaloids, see: Huang L., Xue Z., "The Alkaloids-Chemistry and Pharmacology," Vol. 23, ed. by Brossi A., Academic Press, Orland, 1984, pp. 157-226; Miah M. A. J., Hudlicky T., Reed J. W., "The Alkaloids-Chemistry and Biology," Vol. 51, ed. by Cordell G. A., Academic Press, San Diego, 1998, pp. 199-269.
2. For reviews of the Cephalotaxus alkaloids, see: Huang L., Xue Z., "The Alkaloids-Chemistry and Pharmacology," Vol. 23, ed. by Brossi A., Academic Press, Orland, 1984, pp. 157-226; Miah M. A. J., Hudlicky T., Reed J. W., "The Alkaloids-Chemistry and Biology," Vol. 51, ed. by Cordell G. A., Academic Press, San Diego, 1998, pp. 199-269.
3. Smith C. R., Jr., Mikolajczak K. L., Powell R. G., "Anticancer Agents Based on Natural Product Models," ed. by Cassady J. M., Douros J. D., Academic Press, New York, 1980, pp. 391-416.
4. For the total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975);
5. b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975);
6. Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986);
7. Kuehne M. E., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3450 (1988);
8. e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990);
9. f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993);
10. g) Lin X., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996);
11. h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
12. For the synthesis of optically active cephalotaxine, see: a) Isono N., Mori M., J. Org. Chem., 60, 115-119 (1995);
13. b) Nagasaka T., Sato H., Saeki S., Tetrahedron: Asymmetry, 8, 191-194 (1997).
14. A part of this work has appeared as preliminary communications: Ikeda M., Matsubayashi K., Imoto T., Kitao K., Ishibashi H., Sato T., Heterocycles, 38, 1237-1240 (1994); Ikeda M., Akamatsu S., Kugo Y., Sato T., ibid., 42, 155-158 (1996).
15. A part of this work has appeared as preliminary communications: Ikeda M., Matsubayashi K., Imoto T., Kitao K., Ishibashi H., Sato T., Heterocycles, 38, 1237-1240 (1994); Ikeda M., Akamatsu S., Kugo Y., Sato T., ibid., 42, 155-158 (1996).
16. Ikeda M., Hirose K., El Bialy S. A. A., Sato T., Yakura T., Bayomi S. M. M., Chem. Pharm Bull., 46, 1084-1089 (1998).
17. Seebach D., Boes M., Naef R., Schweizer W. B., J. Am. Chem. Soc., 105, 5390-5398 (1983).
18. Dallacker F., Adolphen G., Justus Liebigs Ann. Chem., 691, 134-137 (1966).
19. Ishibashi H., Ikeda M., Choi H. D., Nakagawa H., Ueda Y., Tamura Y., Chem. Pharm. Bull., 33, 5310-5315 (1985), and references cited therein.
20. Harayama T., Akiyama T., Nakano Y., Chem. Pharm. Bull., 45, 1723-1725 (1997).
21. Similar dehalogenation was observed in the Heck reaction of 2,3-dihydro-N-(2-iodobenzyl)-6-phenyl-4-pyridone, see: Comins D. L., Joseph S. P., Zhang Y., Tetrahedron Lett., 37, 793-796 (1996).
22. McMurry J. E., Andrus A., Ksander G. M., Musser J. H., Johnson M. A., J. Am. Chem. Soc., 101, 1330-1332 (1979).
23. 3∩