Use of epoxidation and epoxide opening reactions for the synthesis of highly functionalized 1-oxaspiro[4.5]decan-2-ones and related compounds

Tetrahedron

Volumn 59, Issue 40, 2003, Pages 7949-7960

  Eipert, Martin ^a   Maichle Mössmer, Cäcilia ^a   Maier, Martin E ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

1 oxaspiro 4.5 decan 2 ones; Epoxidation; Michael acceptor

Indexed keywords

3 AZIDO 10 [[TERT BUTYL(DIMETHYL)SILYL]OXY] 1 OXASPIRO[4.5]DEC 6 EN 2 ONE; 3' [(TRIMETHYLSILYL)OXY]DIHYDRO 5H SPIRO(FURAN 2,2' [7]OXABICYCLO[4.1.0]HEPTAN) 5 ONE; 3' [[TERT BUTYL(DIMETHYL)SILYL]OXY]DIHYDRO 5H SPIRO(FURAN 2,2' [7]OXABICYCLO[4.1.0]HEPTAN) 5 ONE; 3A [3 [[TERT BUTYL(DIMETHYL)SILYL]OXY]PROPYL] 2,2 DIMETHYL 7,7A DIHYDRO 1,3 BENZODIOXOL 4(3AH) ONE; 6 BROMO 10 HYDROXY 1 OXASPIRO[4.5]DECAN 2 ONE; 6 BROMO 10 [(TRIMETHYLSILYL)OXY] 1 OXASPIRO[4.5]DECAN 2 ONE; 6 BROMO 10 [[TERT BUTYL(DIMETHYL)SILYL]OXY] 1 OXASPIRO[4.5]DECAN 2 ONE; 7 BROMO 10 [[TERT BUTYL(DIMETHYL)SILYL]OXY] 6 HYDROXY 1 OXASPIRO[4.5]DECAN 2 ONE; ALCOHOL DERIVATIVE; ANTIFUNGAL AGENT; CYCLOHEXENE DERIVATIVE; EPOXIDE; ETHYL 3 (2 HYDROXY 7 OXABICYCLO[4.1.0]HEPT 1 YL)PROPANOATE; ETHYL 3 (6 HYDROXYCYCLOHEX 1 EN 1 YL)PROPANOATE; ETHYL 3 [2 (ACETOXY) 1,6 DIHYDROXYCYCLOHEXYL]PROPANOATE; ISOPROPYL 3 (1,2,6 TRIHYDROXYCYCLOHEXYL)PROPANOATE; KETONE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; DRUG SYNTHESIS; EPOXIDATION; PRIORITY JOURNAL;

EID: 0141517574     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.010     Document Type: Article

References (39)

1. Su J.Y., Zhong Y.L., Zeng L.M. J. Nat. Prod. 56:1993;288.
2. Cimanga K., Hermans N., Apers S., Van Miert S., Van den Heuvel H., Claeys M., Pieters L., Vlietinck A. J. Nat. Prod. 66:2003;97-102.
3. (a) Paquette L.A., Bibart R.T., Seekamp C.K., Kahane A.L. Org. Lett. 3:2001;4039-4041
4. (b) Paquette L.A., Owen D.R., Bibart R.T., Seekamp C.K., Kahane A.L., Lanter J.C., Corral M.A. J. Org. Chem. 66:2001;2828-2834.
5. Michaut M., Santelli M., Parrain J.-L. Tetrahedron Lett. 44:2003;2157-2159.
6. Taylor S.K., Chmiel N.H., Mann E.E., Silver M.E., Vyvyan J.R. Synthesis. 1998;1009-1014.
7. (a) Wipf P., Kim Y., Fritch P.C. J. Org. Chem. 58:1993;7195-7203
8. (b) McKillop A., McLaren L., Taylor R.J.K., Watson R.J., Lewis N.J. J. Chem. Soc., Perkin Trans. 1. 1996;1385-1393
9. (c) Mukhopadhyay T., Bhat R.G., Roy K., Vijayakumar E.K.S., Ganguli B.N. J. Antibiot. 51:1998;439-441.
10. Isolation: (a) Tanaka M., Nara F., Suzuki-Konagai K., Hosoya T., Ogita T. J. Am. Chem. Soc. 119:1997;7871-7872 (b) Nara F., Tanaka M., Masuda-Inoue S., Yamasato Y., Doi-Yoshioka H., Suzuki-Konagai K., Kumakura S., Ogita T. J. Antibiot. 52:1999;531-535.
11. Isolation: (a) Tanaka M., Nara F., Suzuki-Konagai K., Hosoya T., Ogita T. J. Am. Chem. Soc. 119:1997;7871-7872 (b) Nara F., Tanaka M., Masuda-Inoue S., Yamasato Y., Doi-Yoshioka H., Suzuki-Konagai K., Kumakura S., Ogita T. J. Antibiot. 52:1999;531-535.
12. Synthetic studies and analogs: (a) Izuhara T., Katoh T. Tetrahedron Lett. 41:2000;7651-7655 (b) Saito S., Tanaka N., Fujimoto K., Kogen H. Org. Lett. 2:2000;505-506 (c) Runcie K.A., Taylor R.J.K. Org. Lett. 3:2001;3237-3239 (d) Hoye T.R., Tennakoon M.A. Org. Lett. 2:2000;1481-1483 (e) Arenz C., Giannis A. Angew. Chem. 112:2000;1498-1500. Angew. Chem. Int. Ed. 2000, 39, 1440-1442 (f) Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y. Tetrahedron Lett. 43:2002;4825-4828 (g) Takagi R., Miyanaga W., Tamura Y., Ohkata K. Chem. Commun. 2002;2096-2097 (h) Murray L.M., O'Brien P., Taylor R.J.K. Org. Lett. 5:2003;1943-1946.
13. Synthetic studies and analogs: (a) Izuhara T., Katoh T. Tetrahedron Lett. 41:2000;7651-7655 (b) Saito S., Tanaka N., Fujimoto K., Kogen H. Org. Lett. 2:2000;505-506 (c) Runcie K.A., Taylor R.J.K. Org. Lett. 3:2001;3237-3239 (d) Hoye T.R., Tennakoon M.A. Org. Lett. 2:2000;1481-1483 (e) Arenz C., Giannis A. Angew. Chem. 112:2000;1498-1500. Angew. Chem. Int. Ed. 2000, 39, 1440-1442 (f) Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y. Tetrahedron Lett. 43:2002;4825-4828 (g) Takagi R., Miyanaga W., Tamura Y., Ohkata K. Chem. Commun. 2002;2096-2097 (h) Murray L.M., O'Brien P., Taylor R.J.K. Org. Lett. 5:2003;1943-1946.
14. Synthetic studies and analogs: (a) Izuhara T., Katoh T. Tetrahedron Lett. 41:2000;7651-7655 (b) Saito S., Tanaka N., Fujimoto K., Kogen H. Org. Lett. 2:2000;505-506 (c) Runcie K.A., Taylor R.J.K. Org. Lett. 3:2001;3237-3239 (d) Hoye T.R., Tennakoon M.A. Org. Lett. 2:2000;1481-1483 (e) Arenz C., Giannis A. Angew. Chem. 112:2000;1498-1500. Angew. Chem. Int. Ed. 2000, 39, 1440-1442 (f) Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y. Tetrahedron Lett. 43:2002;4825-4828 (g) Takagi R., Miyanaga W., Tamura Y., Ohkata K. Chem. Commun. 2002;2096-2097 (h) Murray L.M., O'Brien P., Taylor R.J.K. Org. Lett. 5:2003;1943-1946.
15. Synthetic studies and analogs: (a) Izuhara T., Katoh T. Tetrahedron Lett. 41:2000;7651-7655 (b) Saito S., Tanaka N., Fujimoto K., Kogen H. Org. Lett. 2:2000;505-506 (c) Runcie K.A., Taylor R.J.K. Org. Lett. 3:2001;3237-3239 (d) Hoye T.R., Tennakoon M.A. Org. Lett. 2:2000;1481-1483 (e) Arenz C., Giannis A. Angew. Chem. 112:2000;1498-1500. Angew. Chem. Int. Ed. 2000, 39, 1440-1442 (f) Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y. Tetrahedron Lett. 43:2002;4825-4828 (g) Takagi R., Miyanaga W., Tamura Y., Ohkata K. Chem. Commun. 2002;2096-2097 (h) Murray L.M., O'Brien P., Taylor R.J.K. Org. Lett. 5:2003;1943-1946.
16. Synthetic studies and analogs: (a) Izuhara T., Katoh T. Tetrahedron Lett. 41:2000;7651-7655 (b) Saito S., Tanaka N., Fujimoto K., Kogen H. Org. Lett. 2:2000;505-506 (c) Runcie K.A., Taylor R.J.K. Org. Lett. 3:2001;3237-3239 (d) Hoye T.R., Tennakoon M.A. Org. Lett. 2:2000;1481-1483 (e) Arenz C., Giannis A. Angew. Chem. 112:2000;1498-1500. Angew. Chem. Int. Ed. 2000, 39, 1440-1442 (f) Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y. Tetrahedron Lett. 43:2002;4825-4828 (g) Takagi R., Miyanaga W., Tamura Y., Ohkata K. Chem. Commun. 2002;2096-2097 (h) Murray L.M., O'Brien P., Taylor R.J.K. Org. Lett. 5:2003;1943-1946.
17. Synthetic studies and analogs: (a) Izuhara T., Katoh T. Tetrahedron Lett. 41:2000;7651-7655 (b) Saito S., Tanaka N., Fujimoto K., Kogen H. Org. Lett. 2:2000;505-506 (c) Runcie K.A., Taylor R.J.K. Org. Lett. 3:2001;3237-3239 (d) Hoye T.R., Tennakoon M.A. Org. Lett. 2:2000;1481-1483 (e) Arenz C., Giannis A. Angew. Chem. 112:2000;1498-1500. Angew. Chem. Int. Ed. 2000, 39, 1440-1442 (f) Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y. Tetrahedron Lett. 43:2002;4825-4828 (g) Takagi R., Miyanaga W., Tamura Y., Ohkata K. Chem. Commun. 2002;2096-2097 (h) Murray L.M., O'Brien P., Taylor R.J.K. Org. Lett. 5:2003;1943-1946.
18. Synthetic studies and analogs: (a) Izuhara T., Katoh T. Tetrahedron Lett. 41:2000;7651-7655 (b) Saito S., Tanaka N., Fujimoto K., Kogen H. Org. Lett. 2:2000;505-506 (c) Runcie K.A., Taylor R.J.K. Org. Lett. 3:2001;3237-3239 (d) Hoye T.R., Tennakoon M.A. Org. Lett. 2:2000;1481-1483 (e) Arenz C., Giannis A. Angew. Chem. 112:2000;1498-1500. Angew. Chem. Int. Ed. 2000, 39, 1440-1442 (f) Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y. Tetrahedron Lett. 43:2002;4825-4828 (g) Takagi R., Miyanaga W., Tamura Y., Ohkata K. Chem. Commun. 2002;2096-2097 (h) Murray L.M., O'Brien P., Taylor R.J.K. Org. Lett. 5:2003;1943-1946.
19. Synthetic studies and analogs: (a) Izuhara T., Katoh T. Tetrahedron Lett. 41:2000;7651-7655 (b) Saito S., Tanaka N., Fujimoto K., Kogen H. Org. Lett. 2:2000;505-506 (c) Runcie K.A., Taylor R.J.K. Org. Lett. 3:2001;3237-3239 (d) Hoye T.R., Tennakoon M.A. Org. Lett. 2:2000;1481-1483 (e) Arenz C., Giannis A. Angew. Chem. 112:2000;1498-1500. Angew. Chem. Int. Ed. 2000, 39, 1440-1442 (f) Fujioka H., Kotoku N., Sawama Y., Nagatomi Y., Kita Y. Tetrahedron Lett. 43:2002;4825-4828 (g) Takagi R., Miyanaga W., Tamura Y., Ohkata K. Chem. Commun. 2002;2096-2097 (h) Murray L.M., O'Brien P., Taylor R.J.K. Org. Lett. 5:2003;1943-1946.
20. Drutu I., Njardarson J.T., Wood J.L. Org. Lett. 4:2002;493-496.
21. Hwu J.R., Hakimelahi G.H., Chou C.-T. Tetrahedron Lett. 33:1992;6469-6472.
22. (a) Stork G., Mook R., Biller S.A., Rychnovsky S.D. J. Am. Chem. Soc. 105:1983;3741-3742
23. (b) Wu H.-J., Chao C.-S., Lin C.-C. J. Org. Chem. 63:1998;7687-7693
24. (c) Danishefsky S.J., Myles D.C., Harvey D.F. J. Am. Chem. Soc. 109:1987;862-867.
25. (a) Chong J.M., Sharpless K.B. J. Org. Chem. 50:1985;1560-1563
26. (b) Alvarez E., Nuñez M.T., Martin V.S. J. Org. Chem. 55:1990;3429-3431.
27. Barton D.H.R., Godfrey C.R.A., Morzycki J.W., Motherwell W.B., Ley S.V. J. Chem. Soc., Perkin Trans. 1. 1982;1947-1952.
28. Nicolaou K.C., Montagnon T., Baran P.S., Zhong Y.-L. J. Am. Chem. Soc. 124:2002;2245-2258.
29. Dunlap N.K., Sabol M.R., Watt D.S. Tetrahedron Lett. 25:1984;5839-5842.
30. Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 216758 ( 25 ), CCDC 216759 ( 37 ). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
31. Evans D.A., Britton T.C., Ellman J.A., Dorow R.L. J. Am. Chem. Soc. 112:1990;4011-4030.
32. Pellissier H., Michellys P.-Y., Santelli M. J. Org. Chem. 62:1997;5588-5591.
33. de Sousa S.E., Kee A., O'Brien P., Watson S.T. Tetrahedron Lett. 40:1999;387-390.
34. Hoveyda A.H., Evans D.A., Fu G.C. Chem. Rev. 93:1993;1307-1370.
35. Sasaki M., Tanino K., Hirai A., Miyashita M. Org. Lett. 5:2003;1789-1791. and references cited therein.
36. Chini M., Crotti P., Flippin L.A., Gardelli C., Macchia F. J. Org. Chem. 57:1992;1713-1718.
37. Alvarez E., Nuñez M.T., Martin V.S. J. Org. Chem. 55:1990;3429-3431.
38. Paruch E., Ciunik Z., Wawrzeńczyk C., Eur. J. Org. Chem. 1998;2677-2682.
39. Lochyński S., Fra̧ckowiak B., Olejniczak T., Ciunik Z., Wawrzeńczyk C. Tetrahedron: Asymmetry. 13:2002;1761-1767.