Efficient synthesis of [3H]-sanglifehrin A via selective oxidation/reduction of alcohols at C31 and C35

Journal of Organic Chemistry

Volumn 70, Issue 23, 2005, Pages 9588-9590

  Wagner, Jürgen ^a   Andres, Hendrik ^a   Rohrbach, Stefan ^a   Wagner, Dieter ^a   Oberer, Lukas ^a   France, Julien ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; IMMUNOLOGY; LITHIUM COMPOUNDS; OXIDATION; PHARMACOKINETICS; REDUCTION; SYNTHESIS (CHEMICAL); TRITIUM;

CYCLOPHILIN A; PHARMACOKINETIC PROPERTIES; SANGLIFEHRIN A;

PROTEINS;

SANGLIFEHRIN A; ALCOHOL DERIVATIVE; LACTONE; RADIOISOTOPE; REDUCING AGENT; SPIRO COMPOUND; TRITIUM;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; DRUG ISOLATION; DRUG SELECTIVITY; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; STRUCTURE ANALYSIS; SYNTHESIS; CHEMISTRY; HYDROLYSIS;

ALCOHOLS; HYDROLYSIS; LACTONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RADIOISOTOPES; REDUCING AGENTS; SPIRO COMPOUNDS; TRITIUM;

EID: 27744570888     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051112h     Document Type: Article

References (26)

1. (a) Sanglier, J.-J.; Quesniaux, V.; Fehr, T.; Hofmann, H.; Mahnke, M.; Memmert, K.; Schuler, W.; Zenke, G.; Gschwind, L.; Maurer, C.; Schilling, W. J. Antibiot. 1999,52, 466.
2. (b) Fehr, T.; Kallen, J.; Oberer, L.; Sanglier, J.-J.; Schilling, W. J. Antibiot. 1999, 52, 474.
3. Zenke, G.; Strittmatter, U.; Fuchs, S.; Quesniaux, V. F. J.; Brinkmann, V.; Schuler, W.; Zurini, M.; Enz, A.; Billich, A.; Sanglier, J.-J.; Fehr, T. J. Immunol. 2001, 166, 7165-7171.
4. (a) Bänteli, R.; Brun, I.; Hall, P.; Metternich, R. Tetrahedron Lett. 1999, 40, 2109-2112.
5. (b) Hall, P.; Brun, I.; Denni, D.; Metternich, R. Synlett 2000, 3, 315-318.
6. (c) Nicolaou, K. C.; Ohshima, T.; Murphy, F.; Barluenga, S.; Xu, J.; Winssinger, N. Chem. Commun. 1999, 9, 809.
7. (d) Paquette, L. A.; Konetzki, I.; Duan, M. Tetrahedron Lett. 1999, 40, 7441-7444.
8. (e) Duan, M.; Paquette, L. A. Tetrahedron Lett. 2000, 41, 3789-3792.
9. (f) Gurjar, M. K.; Chaudhuri, S. R. Tetrahedron Lett. 2002, 43, 2435-2438.
10. (g) Metternich, R.; Denni, D.; Thai, B.; Sedrani, R. J. Org. Chem. 1999, 64, 9632-9639.
11. (a) Nicolaou, K. C.; Xu, J.; Murphy, F.; Barluenga, S.; Baudoin, O.; Wei, H.-X.; Gray, D. L. F.; Ohshima, T. Angew. Chem., Int. Ed. 1999, 38, 2447-2451.
12. (b) Nicolaou, K. C.; Murphy, F.; Barluenga, S.; Ohshima, T.; Wei, H.; Xu, J.; Gray, D. L. F.; Baudoin, O. J. Am. Chem. Soc. 2000, 122, 3830-3838.
13. (a) Duan, M.; Paquette, L. A. Angew. Chem., Int. Ed. 2001, 40, 3632-3636.
14. (b) Paquette, L. A.; Duan, M.; Konetzki, I.; Kempmann, C. J. Am. Chem. Soc. 2002, 124, 4257-4270.
15. For rapamycin, see: Curran, D. P.; Somayajula, K. V.; Yu, H. Tetrahedron Lett. 1992, 33, 2295-2298.
16. (a) For rapamycin analogues, see: Mönius, Th.; Voges, R.; Mahnke, M.; Burtscher, P.; Metz, Y.; Guenat, Ch. J. Labelled Compd. Radiopharm. 1999, 42, 29-41.
17. (b) For cyclosporine analogues, see: Mönius, Th.; Voges, R.; Susan, A.; Jones, L.; Tarapata, R.; Shapiro, M.; Jarema, M.A. C. Synth. Appl. Isot. Labeled Compd. 1991, 149-154.
18. (c) For a review, see: Mönius, Th.; Baumann, K.; Bulusu, M.; Schweitzer, A.; Voges, R. Synth. Appl. Isot. Labeled Compd. 2001, 424-429.
19. (a) Dess, B. D.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
20. (b) Dess, B. D.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
21. Andres, H.; Morimoto, H.; Williams, P. G. J. Chem. Soc., Chem. Commun. 1990, 8, 627-628.
22. Andres, H.; Morimoto, H.; Williams, P. G. Synthesis and Applications of Isotopically Labelled Compounds; Buncel, E., Kabalka, G. W., Eds.; Elsevier Science Publishers: New York, 1991.
23. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
24. Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538.
25. (a) Leclaire, M.; Jean, P. Bull. Soc. Chim. Fr. 1996, 133, 801-803.
26. (b) Krief, A.; Surleraux, D. Synlett 1991, 273-275.