Total synthesis of thiostrepton. Assembly of key building blocks and completion of the synthesis

Journal of the American Chemical Society

Volumn 127, Issue 31, 2005, Pages 11176-11183

  Nicolaou, K C ^a   Zak, Mark ^a   Safina, Brian S ^a   Estrada, Anthony A ^a   Lee, Sang Hyup ^a   Nevalainen, Marta ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; SYNTHESIS (CHEMICAL);

BUILDING BLOCKS; MACROCYCLES; QUINALDIC ACID; THIOSTREPTON;

ANTIBIOTICS;

MACROCYCLIC COMPOUND; NATURAL PRODUCT; PEPTIDE DERIVATIVE; PIPERIDINE DERIVATIVE; QUINALDIC ACID; TETRAHYDROPYRIDINE; THIAZOLE DERIVATIVE; THIOSTREPTON; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANTI-BACTERIAL AGENTS; MODELS, MOLECULAR; THIOSTREPTON;

EID: 23744439852     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052934z     Document Type: Article

References (17)

1. Nicolaou, K. C.; Safina, B. S.; Zak, M.; Lee, S. H.; Nevalainen, M.; Bella, M.; Estrada, A. A.; Funke, C.; Zécri, F. J.; Bulat, S. J. Am. Chem. Soc. 2005. 127, http://dx.doi.org/10.1021/ja0529337.
2. (a) Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378-1382.
3. (b) Furlan, R. L. E.; Mata, E. G.; Mascaretti, O. A. J. Chem. Soc., Perkin Trans. 1 1998, 355-358.
4. (c) Furlan, R. L. E.; Mata, E. G.; Mascaretti, O. A.; Pena, C; Coba, M. P. Tetrahedron 1998, 54, 13023-13034.
5. (d) Furlan, R. L. E.; Mascaretti, O. A. Aldrichim. Acta 1997, 30, 55-69.
6. (e) Furlan, R. L. E.; Mata, E. G.; Mascaretti, O. A. Tetrahedron Lett. 1996, 37, 5229-5232.
7. (a) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
8. (b) Nicolaou, K. C.; Patron, A. P.; Ajito, K.; Richter, P. K.; Khatuya, H.; Bertinato, P.; Miller, R. A.; Tomaszewski, M. J. Chem. Eur. J. 1996, 2, 847-868.
9. (a) de la Torre, B. G.; Torres, J. L.; Bardaji, E.; Clapés, P.; Xaus, N.; Jorba, X.; Calvet, S.; Albericio, F.; Valencia, G. J. Chem. Soc., Chem. Commun. 1990, 965-967.
10. (b) For a review on the use and removal of allylic protecting groups, see: Guibé, F. Tetrahedron 1998, 54, 2967-3042.
11. Sinha, S. C.; Dutta, S.; Sun, J. Tetrahedron Lett. 2000, 41, 8243-8246.
12. (a) Keinan, E.; Gleize, P. A. Tetrahedron Lett. 1982, 23, 477-480.
13. (b) Four, P.; Guibé, F. Tetrahedron Lett. 1982, 23, 1825-1828.
14. Kessler, H.; Siegmeier, R. Tetrahedron Lett. 1983, 24, 281-282.
15. For a study on the structure and chemistry of dehydroamino acids, sec: Crisma, M.; Formaggio, F.; Toniolo, C.; Yoshikawa, T.; Wakamiya, T. J. Am. Chem. Soc. 1999, 121, 3272-3278.
16. The stereospecific elimination of the TES-protected alcohol to provide the corresponding Z olefin was expected from the results of a previous model study. See Scheme 9B in the preceding article.
17. Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak. M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941-1945.