A short and efficient synthesis of (-)-4a,5-dihydrostreptazolin

Synlett

Volumn , Issue 1, 2000, Pages 122-124

  Cossy, Janine ^a   Pévet, Isabelle ^a   Meyer, Christophe ^a  

^a CNRS   (France)

Author keywords

( ) 4a,5 dihydrostreptazolin; D glyceraldehyde acetonide; Radical cyclization; Ring closing metathesis; Total synthesis

Indexed keywords

4A,5 DIHYDROSTREPTAZOLIN; ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0342514540     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Drautz, H.; Zähner, H.; Kupfer, E.; Keller-Schierlein, W. Helv. Chim. Acta 1981, 64, 1752-1765.
2. Karrer, A.; Dobler, M. Helv. Chim. Acta 1982, 65, 1432-1435.
3. Kozikowski, A.P.; Park, P.U. J. Org. Chem. 1990, 55, 4668-4682.
4. Flann, C.J.; Overman, L.E. J. Am. Chem. Soc. 1987, 709, 6115-6118.
5. (a) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054-1059.
6. (b) Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1996, 37, 8787-8790.
7. Kratzel, M.; Weigl, A. J. Chem. Soc., Perkin Trans, 1 1997, 1009-1012.
8. Schmid, C.R.; Bryant, J.D. Org. Synth. Coll. 1995, 72, 6-13.
9. (a) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M.D.; Galvez, J.A. Tetrahedron 1997, 53, 1411-1416.
10. (b) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M.D.; Galvez, J.A. Synthesis 1997, 747-749.
11. 8b we have checked that no racemization occurred upon addition of vinylmagnesium chloride onto imine 2. Optically pure (+)-13 was synthesized and alkylated with p-methoxybenzyl bromide. The same
12. Schwab, P.; Grubbs, R.H.; Ziller, J.W. J. Am. Chem. Soc. 1996, 118, 100-110.
13. Stork, G.; Mook Jr, R. J. Am. Chem. Soc. 1987, 109, 2829-2831.
14. Negishi, E-I.; Ay, M.; Gulevich, Y.V.; Noda, Y. Tetrahedron Lett. 1993, 34, 1437-1440.
15. 5b