Total Synthesis of (±)-Catharanthine

Journal of Organic Chemistry

Volumn 50, Issue 17, 1985, Pages 3236-3237

  Raucher, Stanley ^a   Bray, Brian L ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATHARANTHINE;

DRUG SYNTHESIS; NONHUMAN; PRELIMINARY COMMUNICATION; THEORETICAL STUDY;

EID: 0021952662     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00217a052     Document Type: Article

References (13)

1. (1) Previous total syntheses of (±)-catharanthine: (a) Buchi, G.; Kulsa, P.; Ogasawara, K.; Rosati, R. J. Am. Chem. Soc. 1969, 92, 999. (b) Marazano, C.; LeGoff, M. T.; Fourrey, J. L.; Das, B. C. J. Chem. Soc., Chem. Commun. 1981, 389. Relay synthesis: (c) Kutney, J. P.; Bylsma, F. Helv. Chim. Acta 1975, 58,1672. Formal total syntheses: (d) Trost, B. M.; Godleski, S. A.; Belletire, J. L. J. Org. Chem. 1979, 44, 2052. (e) Imanishi, T.; Shin, H.; Yagi, N.; Hanaoka, M. Tetrahedron Lett. 1980, 21, 3285.
2. (2) (a) Neuss, N.; Johnson, I. S.; Armstrong, J. G.; Jansen, C. J. Adv. Chemother. 1964, 1, 133. (b) Taylor, W. I.; Farnsworth, N. R. “The Catharanthus Alkaloids ”: Marcell Dekker: New York, 1975. (c) Gerzon, K. In “Anticancer Agents Based on Natural Products Models”, Medicinal Chem.; Cassady, J. M., Douros, J. D., Eds.; Academic Press: New York, 1981; Vol. 16. (d) Jewers, K. Progr. Drug Res. 1981, 25, 275. (e) “Antineoplastic Agents" Remers, W. A., Ed.; Wiley: New York, 1984.
3. (3) Reviews: (a) Kutney, J. P. Lect. Heterocycl. Chem. 1978,4, 59. (b) Potier, P. J. Nat. Prod. (Lloydia) 1980, 43, 72. (c) Lounasmaa, M.; Nemes, A. Tetrahedron 1982, 38, 223.
4. (4) Raucher, S.; Lawrence, R. F. Tetrahedron Lett. 1983, 24, 2927. (5) a-Chloroacetamide photocyclization review: (a) Sundberg, R. J. “Organic Photochemistry”; Padwa, A., Ed.; Marcel Dekker: New York, 1983; Vol. 6. Synthesis of 20-deethylcatharanthine: (b) Sundberg, R. J.; Bloom, J. D. Tetrahedron Lett. 1978, 5157. (c) Sundberg, R. J.; Bloom, J. D. J. Org. Chem. 1980, 45, 3382.
5. 2 336.1838, found 336.1839.
6. (7) Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
7. (8) For the assignment of stereochemistry of carbomethoxy groups at the 7-position of 2-azabicyclo[2.2.2]oct-5-ene derivatives, see: Lawrence, R. F. Ph.D. Thesis, University of Washington, 1984.
8. (9) (a) Sakurai, S.; Shirahata, A.; Sasaki, K.; Hosomi, A. Synthesis 1979, 740. (b) Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. Angew. Chem., Int. Ed. Engl. 1979,18, 612. (c) Seitz, D. E.; Ferreira, L. Synth. Commun. 1979, 9, 931.
9. (10) The O,N-bis(trimethylailyl)acetamide functions as an acid scavenger in this reaction, and the acylation may proceed via the N-silylamine corresponding to 5. For the use of O,N-bis(trimethylsilyl)acetamide in the formation of carbamates from amines and alkyl chloroformates, see: Raucher, S.; Jones, D. S. Synth. Commun., in press.
10. (11) Shaw, E.; Woolley, D. W. J. Biol. Chem. 1953, 203, 979. (12) (a) Szantay, C.; Keve, T.; Bolcskel, H.; Acs, T. Tetrahedron Lett. 1983, 24, 5539. (b) Raucher, S.; Bray, B. L., unpublished results.
11. (13) Scheibye, S.; Pedersen, B. S.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1978, 87, 229.
12. (14) Raucher, S.; Klein, P. Tetrahedron Lett. 1980, 21, 4061. Also see, ref 5b,c.
13. (15) Fellow of the Alfred P. Sloan Foundation (1980–1984). Recipient of NIH Research Career Development Award CA 00864 (1983–1988).