Efficient synthesis of the core structure of muraymycin and caprazamycin nucleoside antibiotics based on a stereochemically revised sulfur ylide reaction

Tetrahedron Asymmetry

Volumn 21, Issue 7, 2010, Pages 763-766

  Spork, Anatol P ^a   Koppermann, Stefan ^a   Dittrich, Birger ^a   Herbst Irmer, Regine ^a   Ducho, Christian ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; CAPRAZAMYCIN NUCLEOSIDE; EPOXIDE; MURAYMYCIN NUCLEOSIDE; NUCLEOSIDE DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 77956487329     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.03.037     Document Type: Article

References (18)

1. Taubes, G. Science 2008, 321, 356-361.
2. Kimura, K.-I.; Bugg, T. D. H. Nat. Prod. Rep. 2003, 20, 252-273.
3. Winn, M.; Goss, R. J. M.; Kimura, K-I.; Bugg, T. D. H. Nat. Prod. Rep. 2010, 27, 279-304.
4. McDonald, L. A.; Barbieri, L. R.; Carter, G. T.; Lenoy, E.; Lotvin, J.; Petersen, P. J.; Siegel, M. M.; Singh, G.; Williamson, R. T. J. Am. Chem. Soc. 2002, 124, 10260-10261.
5. Igarashi, M.; Nakagawa, N.; Doi, S.; Hattori, N.; Naganawa, H.; Hamada, M. J. Antibiot. 2003, 56, 580-583.
6. Hirano, S.; Ichikawa, S.; Matsuda, A. Angew. Chem. 2005, 117, 1888-1890;
7. Angew. Chem., Int. Ed. 2005, 44, 1854-1856.
8. Yamashita, A.; Norton, E.; Petersen, P. J.; Rasmussen, B. A.; Singh, G.; Yang, Y.; Mansour, T. S.; Ho, D. M. Bioorg. Med. Chem. Lett. 2003, 13, 3345-3350.
9. Sarabia, F.; Martín-Ortiz, L. Tetrahedron 2005, 61, 11850-11865.
10. Spork, A. P.; Koppermann, S.; Ducho, C. Synlett 2009, 2503-2507.
11. Sarabia, F.; Martín-Ortiz, L.; López-Herrera, F. J. Org. Lett. 2003, 5, 3927-3930.
12. Valpuesta, M.; Durante, P.; López-Herrera, F. J. Tetrahedron Lett. 1995, 36, 4681-4684.
13. Azzena, F.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron 1995, 51, 13409-13422.
14. 14 which was crucial for arriving at the conclusions reported, was possible. Full crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 770311. These data can be obtained free of charge on application to CCDC, 12, Union Road, Cambridge, CB2 1EZ; fax +44 (1223)336033; or email: deposit@ccdc.cam.ac.uk.
15. Flack, H. D.; Bernardinelli, G. J. Appl. Cryst. 2000, 33, 1143-1148.
16. SHELXL (Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122) was used for structure refinement.
17. Structure solution was achieved with the program SHELXD (Uson, I.; Sheldrick, G. M.; de la Fortelle, E.; Bricogne, G.; Di Marco, S.; Priestle, J. P.; Grüttler, M. G.; Mittl, P. R. E. Structure 1999, 7, 55-63). The asymmetric unit consists of four main molecules with identical absolute configuration, which are accompanied by further seven benzene solvent molecules to give eleven independent molecules.
18. It should be noted that the descriptor of the stereocenter at C-5′ formally changes from (R) to (S) upon reaction with the nitrogen nucleophile at C-6′ due to altered priorities.