Total synthesis of (±)-mycothiazole and formal enantioselective approach

Organic Letters

Volumn 7, Issue 2, 2005, Pages 339-342

  Le Flohic, Alexandre ^a   Meyer, Christophe ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DIBROMOTHIAZOLE; ALCOHOL; MYCOTHIAZOLE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT;

ARTICLE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; RING CLOSING METATHESIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; MOLECULAR STRUCTURE; STEREOISOMERISM; THIAZOLES;

EID: 13444274632     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047603q     Document Type: Article

References (24)

1. Crews, P.; Kakou, Y.; Quiñoà, E. J. Am. Chem. Soc. 1988, 110, 4365-4368.
2. Cutignano, A.; Bruno, I.; Bifulco, G.; Casapullo, A.; Debitus, C.; Gomez-Paloma, L.; Riccio, R. Eur. J. Org. Chem. 2001, 775-778.
3. The results of the National Cancer Institute Human Tumor Cell Line Screen mean graph can be consulted on the Internet at http://dtp.nci.nih.gov (NCS number 647640).
4. The atom numbering has been chosen so that the positions of the thiazole ring (C2/C4/C5) may be designated in the classical fashion.
5. (a) Sugiyama, H.; Yokokawa, F.; Shioiri, T. Org. Lett. 2000, 2, 2149-2152.
6. (b) Sugiyama, H.; Yokokawa, F.; Shioiri, T. Tetrahedron 2003, 59, 6579-6593.
7. Serra, G.; Mahler, G.; Manta, E. Heterocycles 1998, 48, 2035-2048.
8. Rodriguez-Conesa, S.; Candal, P.; Jiménez, C.; Rodriguez, J. Tetrahedron Lett. 2001, 42, 6699-6702.
9. Le Flohic, A.; Meyer, C.; Cossy, J.; Galland, J.-C.; Desmurs, J.-R. Synlett 2003, 667-670.
10. (a) Karsch, S.; Schwab, P.; Metz, P. Syntlett 2002, 2019-2022.
11. (b) Karsch, S.; Freitag, D.; Schwab, P.; Metz, P. Synthesis 2004, 1696-1712.
12. (a) Plietker, B.; Metz, P. Tetrahedron Lett. 1998, 39, 7827-7830.
13. (b) Plietker, B.; Seng, D.; Fröhlich, R.; Metz, P. Eur. J. Org. Chem. 2001, 3669-3676.
14. Reynaud, P.; Robba, M.; Moreau, R. C. Bull. Soc. Chim. Fr. 1962, 1735-1738.
15. Florio, S.; Epifani, E.; Ingrosso, G. Tetrahedron 1984, 40, 4527-4533.
16. No satisfactory conditions were found in order to couple an organometallic species generated at C4 from the substituted 4-bromothiazole 5 with allylic electrophiles incorporating the C14-C19 side chain.
17. 3SnCl, rt).
18. Clive, D. L. J.; Chua Paul, C.; Wang, Z. J. Org. Chem. 1997, 62, 7028-7032.
19. Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175-1176.
20. 2Me and MeOH may have generated traces of HCl, which can catalyze the methanolysis of isocyanates, see: Khoukhi, M.; Vaultier, M.; Banalil, A.; Carboni, B. Synthesis 1996, 483-487.
21. Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439.
22. Determined by chiral HPLC analysis: chiral OD-H column; eluent, hexane; elution rate, 1 mL/min; detection, 230-260 nm; retention times, (S)-enantiomer 48.4 min, (R)-enantiomer 55.5 min.
23. (a) Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321-2336.
24. (b) Cossy, J.; BouzBouz, S.; Pradaux, F.; Willis, C.; Bellosta, V. Synlett 2002, 1595-1606.