Total synthesis of luotonin A

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2723-2724

  Kelly, T Ross ^a   Chamberland, Stephen ^a   Silva, Richard A ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTILEUKEMIC AGENT; LUOTONIN A; PLANT EXTRACT; UNCLASSIFIED DRUG; VASICINONE;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; SPECTRUM;

EID: 0033515803     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00349-4     Document Type: Article

References (13)

1. Ma, Z.; Hano Y.; Nomura T.; Chen, Y. Heterocycles 1997, 46, 541.
2. Slichenmyer, W. J.; Rowinsky, E. K.; Donehower, R. C.; Kaufmann, S. H. J. Nat. Cancer Inst. 1993, 85, 271.
3. For a very recent report of the synthesis of 1 (by a different route) that appeared after this synthesis was complete, see Wang, H; Ganesan, A. Tetrahedron Lett. 1998, 39, 9097.
4. a) Prepared by the method of Onaka, T. Tetrahedron Lett. 1971, 4387. Our conversion of Onaka's f to g employed the procedure in Mori, M.; Kobayashi, H.; Kimura, M.; Ban, Y. Heterocycles 1985, 23, 2803.
5. a) Prepared by the method of Onaka, T. Tetrahedron Lett. 1971, 4387. Our conversion of Onaka's f to g employed the procedure in Mori, M.; Kobayashi, H.; Kimura, M.; Ban, Y. Heterocycles 1985, 23, 2803.
6. b) For the synthesis of the lactim ether used in the synthesis of see Onaka, T. Tetrahedron Lett. 1968, 5711.
7. c) See also Petersen, S.; Tietze, E. Ann. 1959, 623, 166.
8. Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39.
9. 2: C, 65.99; H, 4.03; N, 13.99. Found: C, 65.74; H, 3.98; N, 13.77.
10. For a review of the Friedländer condensation, see Cheng, C. C.; Yan, S. J. Organic Reactions 1982, 25, 37. For a particularly relevant precedent, see Shamma, M.; Novak, L. Tetrahedron 1969, 25, 2275.
11. For a review of the Friedländer condensation, see Cheng, C. C.; Yan, S. J. Organic Reactions 1982, 25, 37. For a particularly relevant precedent, see Shamma, M.; Novak, L. Tetrahedron 1969, 25, 2275.
12. Smith, L. I.; Opie, J. W. Organic Syntheses, Wiley: New York, 1955; Collective Vol. III, p. 56.
13. 1 mp 252 °C (decomp). Spectra of synthetic 1 are identical with those of the natural product.