An asymmetric synthesis of the key precursor to (-)-indolizomycin

Tetrahedron Letters

Volumn 40, Issue 25, 1999, Pages 4639-4642

  Groaning, Michael D ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMOPROPONIC ESTER; ALLYLTRIMETHYLSILANE; ANTIBIOTIC AGENT; CHLORIDE; ESTER DERIVATIVE; INDOLIZOMYCIN; LACTAM DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIDINONE; REAGENT; SILANE DERIVATIVE; SULFOXONIUM METHYLIDE; TITANIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0033580907     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00728-5     Document Type: Article

References (14)

1. 1. (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
2. (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1.
3. 2. (a) Yamashita, F.; Hotta, K.; Kurasawa, S.; Okami, Y.; Umezawa, H. J. Antibiot. 1985, 38, 58.
4. (b) Gomi, S.; Ikeda, D.; Nakamura, H.; Naganawa, H.; Yamashita, F.; Hotta, K.; Kondo, S.; Okami, Y.; Umezawa, H.; Iitaka, Y. J. Antibiot. 1984, 37, 1491.
5. 3. Kim, G.; Chu-Moyer, M. Y.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1993, 115, 30.
6. 4. Resek, J. G.; Meyers, A. I. Tetrahedron Lett. 1995, 36, 7051.
7. 5. Corey, E. J.; Chaykovsky, M. J. J. Am. Chem. Soc. 1965, 87, 1353.
8. 6. (a) Romo, D.; Romine, J. L.; Midura, W.; Meyers, A. I. Tetrahedron 1990, 46, 1936.
9. (b) Meyers, A. I.; Romine, J. L.; Fleming, S. A. J. Am. Chem. Soc. 1989, 110, 7245.
10. 7. Meyers, A. I.; Burgess, L. E. J. Org. Chem. 1991, 56, 2294.
11. 8. A racemic sample of (1α,2α,5α)-(-)-2-(2-propenyl)-4-oxo-3-azabicyclo[3.1.0 ]hexane-3-propanoic acid methyl ester was provided by Professor Danishefsky.
12. 9. Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36.
13. 10. Combustion analyses were performed by Atlantic Microlabs Inc., Norcross, GA. High resolution mass spectra were obtained from U.C.-Riverside.
14. +) requires 224.1293).