Rapid assembly of the 1-azabicyclo[3.1.0]hexane skeleton of ficellomycin

Synlett

Volumn , Issue 12, 2004, Pages 2212-2214

  Paumier, D ^a   Garcia, M ^b   Shipman, M ^a,b   Muir, J C ^c  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

1,2 Azido alcohols; Antibiotics; Aziridines; Conjugate addition reactions; Polymer supported triphenylphosphine

Indexed keywords

1 AZABICYCLO[3.1.0]HEXANE; 1,2 AZIDO ALCOHOL; ALCOHOL DERIVATIVE; AMINE; ANTIBIOTIC AGENT; AZIRIDINE; BICYCLO COMPOUND; ESTER; FICELLOMYCIN; HEXANE; NATURAL PRODUCT; POLYMER; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STAUDINGER REACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 5644253214     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831313     Document Type: Article

References (16)

1. Argoudelis, A. D.; Reusser, F.; Whaley, H. A.; Baczynskyj, L.; Mizsak, S. A.; Wnuk, R. J. J. Antibiot. 1976, 29, 1001.
2. Reusser, F. Biochemistry 1977, 16, 3406.
3. Kuo, M-S.; Yurek, D. A.; Mizsak, S. A. J. Antibiot. 1989, 42, 357.
4. For a review, see Hodgkinson, T. J.; Shipman, M. Tetrahedron 2001, 57, 4467.
5. Zhao, Z. PhD Thesis; University of California: Los Angeles, 1993.
6. For some alternative approaches to 1-azabicyclo[3.1.0]-hexanes, see: (a) Buyle, R. Chem. Ind. (London) 1966, 195.
7. (b) Laurent, D. A. Chimia 1976, 30, 274.
8. (c) Hudlicky, T.; Frazier, J. O.; Seoane, G.; Tiedje, M.; Seoane, A.; Kwart, L. D.; Beal, C. J. J. Am. Chem. Soc. 1986, 108, 3755.
9. (d) Mulzer, J.; Becker, R.; Brunner, E. J. Am. Chem. Soc. 1989, 111, 7500.
10. (e) Sasaki, M.; Yudin, A. K. J. Am. Chem. Soc. 2003, 125, 14242.
11. Intramolecular conjugate additions involving aziridine nucleophiles are known. For example, see: (a) Moran, E. J.; Tellew, J. E.; Zhao, Z.; Armstrong, R. W. J. Org. Chem. 1993, 58, 7848.
12. (b) Coleman, R. S.; Li, J.; Navarro, A. Angew. Chem. Int. Ed. 2001, 40, 1736.
13. (c) ref. 5.
14. 2, 3 h, r.t.), which was used directly in the olefination reaction without purification.
15. Hiebl, J.; Kollmann, H.; Rovenszky, F.; Winkler, K. J. Org. Chem. 1999, 64, 1947.
16. +].