Synthesis of enantiopure (S)-7-hydroxy-3-amino-3,4-dihydro-2H-1-benzopyran en route to (+)-scyphostatin

Tetrahedron Letters

Volumn 48, Issue 9, 2007, Pages 1523-1526

  Pitsinos, Emmanuel N ^a   Moutsos, Vassilios I ^a   Vageli, Olga ^a  

^a Institute of Physical Chemistry   (Greece)

Author keywords

Bis(trifluoroacetoxy)iodo benzene; Aminochroman; p Quinol

Indexed keywords

4 (2 ACETOXYBENZYL)OXAZOLIDIN 2 ONE; 4 QUINOL ACETATE; 7 HYDROXY 3 AMINO 3,4 DIHYDRO 2H 1 BENZOPYRAN; BENZOPYRAN DERIVATIVE; NATURAL PRODUCT; OXAZOLIDINONE DERIVATIVE; PHENOL; RESORCINOL; SCYPHOSTATIN; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 33846696072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.006     Document Type: Article

References (32)

1. Podona T., Guardiola-Lemaitre B., Caignard D.H., Adam G., Pfeiffer B., Renard P., and Guillaumet G. J. Med. Chem. 37 (1994) 1779-1793
2. Boyé S., Pfeiffer B., Renard P., Rettori M.-C., Guillaumet G., and Viaud M.-C. Bioorg. Med. Chem. 7 (1999) 335-341
3. Hammarberg E., Nordvall G., Leideborg R., Nylöf M., Hanson S., Johansson L., Thorberg S.-O., Tolf B.-R., Jerning E., Svantesson G.T., Mohell N., Ahlgren C., Westlind-Danielsson A., Csöregh I., and Johansson R. J. Med. Chem. 43 (2000) 2837-2850
4. Holmberg P., Sohn D., Leideborg R., Cardirola P., Zlatoidsky P., Hanson S., Mohell N., Rosqvist S., Nordvail G., Johansson A.M., and Johansson R. J. Med. Chem. 47 (2004) 3927-3930
5. Holmberg P., Tedenborg L., Rosqvist S., and Johansson A.M. Bioorg. Med. Chem. Lett. 15 (2005) 747-750
6. Hatzenbuhler N.T., Evrard D.A., Harrison B.L., Huryn D., Inghrim J., Kraml C., Mattes J.F., Mewshaw R.E., Zhou D., Hornby G., Lin Q., Smith D.L., Sullivan K.M., Schechter L.E., Beyer C.E., and Andree T.H. J. Med. Chem. 49 (2006) 4785-4789
7. Pitsinos E.N., and Cruz A. Org. Lett. 7 (2005) 2245-2248
8. Wascholowski V., Giannis A., and Pitsinos E.N. ChemMedChem 1 (2006) 718-721
9. Dupau P., Le Gendre P., Bruneau C., and Dixneuf P.H. Synlett 11 (1999) 1832-1834
10. Dupau P., Bruneau C., and Dixneuf P.H. Tetrahedron: Asymmetry 10 (1999) 3467-3471
11. Usse S., Pave G., Guillaumet G., and Viaud-Massuard M.-C. Tetrahedron: Asymmetry 12 (2001) 1689-1694
12. Renaud J.L., Dupau P., Hay A.-E., Guingouain M., Dixneuf P.H., and Bruneau C. Adv. Synth. Catal. 345 (2003) 230-238
13. Pavé G., Usse-Versluys S., Viaud-Massuard M.-C., and Guillaumet G. Org. Lett. 5 (2003) 4253-4256
14. Hamamoto H., Hata K., Nambu H., Shiozaki Y., Tohma H., and Kita Y. Tetrahedron Lett. 45 (2004) 2293-2295
15. Lal K., Ghosh S., and Salomon R.G. J. Org. Chem. 52 (1987) 1072-1078
16. Paquette L.A., Schulze M.M., and Bolin D.G. J. Org. Chem. 59 (1994) 2043-2051
17. Shi Z., and He C. J. Am. Chem. Soc. 126 (2004) 13596-13597
18. Mori K., Yamamura S., and Nishiyama S. Tetrahedron 57 (2001) 5533-5542
19. Magdziak D., Meek S.J., and Pettus T.R.R. Chem. Rev. 104 (2004) 1383-1429
20. Hara H., Inoue T., Endoh M., Nakamura H., Takahashi H., and Hoshino O. Heterocycles 42 (1996) 445-451
21. Green R., Taylor P.J.M., Bull S.D., James T.D., Mahon M.F., and Merritt A.T. Tetrahedron: Asymmetry 14 (2003) 2619-2623
22. Goodwin S., and Witkop B. J. Am. Chem. Soc. 79 (1957) 179-185
23. Although to the best of our knowledge this is the first example where such a transformation is exploited synthetically, an intermolecular version has been observed as an undesired reaction: see:. Evans D.A., Chapman K.T., and Bisaha J. J. Am. Chem. Soc. 110 (1988) 1238-1256
24. Similar reactions employing cyclic carbonates have been reported; see for example:. Couladouros E.A., and Mihou A.P. Tetrahedron Lett. 40 (1999) 4861-4862
25. For other approaches to 3,4-dihydro-2H-1-benzopyrans via intramolecular cyclizations involving the formation of an O-C-2 bond see:. Stafford J.A., and Valvano N.L. J. Org. Chem. 59 (1994) 4346-4349
26. Li L., and Chan T.H. Org. Lett. 3 (2001) 739-741
27. Zaveri N.T. Org. Lett. 3 (2001) 843-846
28. Trost B.M., Shen H.C., Dong L., and Surivet J.-P. J. Am. Chem. Soc. 125 (2003) 9276-9277
29. Ishizuka T., and Kunieda T. Tetrahedron Lett. 28 (1987) 4185-4188
30. A total synthesis of (+)-scyphostatin has already been reported:. Inoue M., Yokota W., Murugesh M.G., Izuhara T., and Katoh T. Angew. Chem., Int. Ed. 43 (2004) 4207-4209
31. Kim K., Parang K., Lau O.D., and Cole P.A. Bioorg. Med. Chem. 8 (2000) 1263-1268
32. Barrett A.G.M., Henessy A.J., Le Vézouët R., Procopiou P.A., Seale P.W., Stefaniak S., Upton R.J., White A.J.P., and Williams D.J. J. Org. Chem. 69 (2004) 1028-1037