Total synthesis of (+)-streptazolin

Chemical Communications

Volumn , Issue 7, 2000, Pages 569-570

  Huang, Shenlin ^a   Comins, Daniel L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; NATURAL PRODUCT; STREPTAZOLIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; DRUG CONFORMATION; DRUG SYNTHESIS; ISOMERISM; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034616331     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001425g     Document Type: Article

References (19)

1. H. Drautz, H. Zächner, E. Kupfer and W. Keller-Schierlein, Helv. Chim. Acta, 1981, 64, 1752.
2. A. Karrer and M. Dobler, Helv. Chim. Acta, 1982, 65, 1432.
3. S. Grabley, H. Kluge and H.-U. Hoppe, Angew. Chem., Int. Ed. Engl., 1987, 26, 664.
4. A. P. Kozikowski and P. Park, J. Am. Chem. Soc., 1985, 107, 1763; A. P. Kozikowski and P. Park, J. Org. Chem., 1990, 55, 4668.
5. A. P. Kozikowski and P. Park, J. Am. Chem. Soc., 1985, 107, 1763; A. P. Kozikowski and P. Park, J. Org. Chem., 1990, 55, 4668.
6. C. J. Flann and L. E. Overman, J. Am. Chem. Soc., 1987, 109, 6115.
7. H. Yamada, S. Aoyagi and C. Kibayashi, J. Am. Chem. Soc., 1996, 118, 1054.
8. D. L. Comins, C. A. Brooks, R. S. Al-awar and R. R. Goehring, Org. Lett., 1999, 1, 229; D. L. Comins, A. H. Libby, R. S. Al-awar and C. J. Foti, J. Org. Chem., 1999, 64, 2184.
9. D. L. Comins, C. A. Brooks, R. S. Al-awar and R. R. Goehring, Org. Lett., 1999, 1, 229; D. L. Comins, A. H. Libby, R. S. Al-awar and C. J. Foti, J. Org. Chem., 1999, 64, 2184.
10. D. L. Comins, J. T. Kuethe, H. Hong, F. J. Lakner, T. E. Concolino and A. L. Rheingold, J. Am. Chem. Soc., 1999, 121, 2651 and references therein.
11. D. L. Commins, S. P. Joseph and R. R. Goehring, J. Am. Chem. Soc., 1994, 116, 4719.
12. S. Nahm and S. M. Weinreb, Tetrahedron Lett., 1981, 22, 3815; T. Shimizu, K. Osako and T. Nakata, Tetrahedron Lett., 1997, 38, 2685 and references therein.
13. S. Nahm and S. M. Weinreb, Tetrahedron Lett., 1981, 22, 3815; T. Shimizu, K. Osako and T. Nakata, Tetrahedron Lett., 1997, 38, 2685 and references therein.
14. Prop-1-ynyllithium was prepared from 1-bromoprop-1-ene and n-butyllithium in THF, see: D. Toussaint and J. Suffert, Org. Synth., 1998, 76, 214.
15. 12 This highly stereoselective reduction is likely a result of a chelation-controlled addition mechanism.
16. D. L. Comins and J. M. Salvador, J. Org. Chem., 1993, 58, 4656.
17. A one-pot reduction of an N-alkyl-2,3-dihydro-4-pyridone to a C-4 axial alcohol using excess L-Selectride has been reported, see: G. Han, M. G. LaPorte, J. J. Folmer, K. M. Werner and S. M. Weinreb, Angew. Chem., 2000, 39, 237.
18. For an example of vinyl bromide formation from a ß-bromo triflate, see: W. Ng and D. Wege, Tetrahedron Lett., 1996, 37, 6797.
19. R. Grigg, J. Heterocycl. Chem., 1994, 31, 631 and references therein.