Synthesis of 1-substituted 2,9,10-trioxatricyclo[4.3.1.0 3,8]decanes

Tetrahedron

Volumn 60, Issue 23, 2004, Pages 5077-5084

  Stanoeva, Elena ^a   He, Weidong ^a   Rocchetti, Maria Teresa ^a   Nguyen Van, Tuyen ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

All cis cyclohexane 1,2,4 triol; Cage orthoesters; Pinner reaction; Resiniferatoxin; Transetherification

Indexed keywords

1 (BUTEN 1 YL) 2,9,10 TRIOXATRICYCLO[4.3.1.0 3,8 ]DECANE; 1 (HEXEN 1 YL) 2,9,10 TRIOXATRICYCLO[4.3.1.0 3,8 ]DECANE; 1 (PENTEN 1 YL) 2,9,10 TRIOXATRICYCLO[4.3.1.0 3,8 ]DECANE; 1 BUTYL 2,9,10 TRIOXATRICYCLO[4.3.1.0 3,8 ]DECANE; 1 NONYL 2,9,10 TRIOXATRICYCLO[4.3.1.0 3,8 ]DECANE; 1 PENTADECYL 2,9,10 TRIOXATRICYCLO[4.3.1.0 3,8 ]DECANE; 1 PHENYL 2,9,10 TRIOXATRICYCLO[4.3.1.0 3,8 ]DECANE; 2,9,10 TRIOXATRICYCLO[4.3.1.0 3,8 ]DECANE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANE; DECANE; RESINIFERATOXIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ETHERIFICATION; EXPERIMENTAL MODEL; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

SYNAPTOLEPIS;

EID: 2442623473     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.04.016     Document Type: Article

References (39)

1. Hergenhahn M., Adolf W., Hecker E. Tetrahedron Lett. 1975;1595-1598
2. Adolf W., Soko B., Hergenhahn M., Hecker E. J. Nat. Prod. 45:1982;347-354
3. Adolf W., Hecker E. Isr. J. Chem. 16:1977;75-83
4. Brooks G., Evans A.T., Aitken A., Evans F.J., Rozk A.F.M., Hammouda F.M., El-Missiry M., Ismail S.E. Phytochemistry. 29:1990;2235-2237
5. Yaga S., Kinjo K., Hayashi H., Matsuo N., Abe F., Yamauchi T. Phytochemistry. 32:1992;141-143
6. Abe F., Iwase Y., Yamauchi T., Kinjo K., Yaga S. Phytochemistry. 44:1997;643-647
7. Kupchan S.M., Shizuri Y., Sumner W.C., Haynes H.R., Leighton A.P., Sickles B.R. J. Org. Chem. 41:1976;3850-3853
8. Appendino G. Gazz. Chim. Ital. 127:1997;461-469
9. Abe F., Iwase Y., Yamauchi T., Kinjo K., Yaga S., Ishi M., Iwahana M. Phytochemistry. 47:1998;833-837
10. He W., Cik M., Lesage A., Van Der Linden I., De Kimpe N., Appendino G., Bracke J., Mathenghe S.G., Mudida F.P., Leysen J.E., Van Puyvelde L. J. Nat. Prod. 63:2000;1185-1187
11. Evans F.J., Soper C.J. J. Nat. Prod. 41:1978;193-233
12. He W., Cik M., Appendino G., Van Puyvelde L., Leysen J.E., De Kimpe N. Mini-Rev. Med. Chem. 2:2002;185-200
13. Appendino G., Szallasi A. Life Sci. 60:1997;681-696
14. Rouhi A.M. Chem. Engng News. 76:1998;31-34
15. Blumberg P.M., Szallasi A. Wood J.N. Capsaicin in the Study of Pain. 1993;45-62 Academic, London
16. Walpole C.S.J., Bevan S., Bloomfield G., Breckenridge R., James I.F., Ritchie T., Szallasi A., Winter J., Wrigglesworth R. J. Med. Chem. 39:1996;2939-2952
17. McDonnell M.E., Zhang S.P., Dubin A.E., Dax S.L. Bioorg. Med. Chem. Lett. 12:2002;1189-1192
18. Adolf W., Hecker E. Z. Naturforsch.; B: Chem. Sci. 48:1993;364-368
19. He W., Cik M., Van Puyvelde L., Van Dun J., Appendino G., Lesage A., Van der Linden I., Leysen J.E., Wouters W., Mathenge S.G., Mudida F.P., De Kimpe N. Bioorg. Med. Chem. 10:2002;3245-3255
20. Wender P.A., Jesudason C.D., Nakahira H., Tamura N., Tebbe A.L., Ueno Y. J. Am. Chem. Soc. 119:1997;12976-12977
21. Nakahira, H.; Tamura, N. Tennen Yuki Toronkai Koen Yoshoshu 38th, Abstracts of Papers, 1996; pp 571-576; Chem. Abstr. 1996, 126, 31505t.
22. Nakahira, H.; Tamura, N. Tennen Yuki Toronkai Koen Yoshoshu 38th, Abstracts of Papers, 1996; pp 571-576; Chem. Abstr. 1996, 126, 31505t.
23. Kupchan S.M. J. Am. Chem. Soc. 77:1955;686-689
24. Kupchan S.M., Johnson S.W., Rajagopalan S. Tetrahedron. 7:1959;47-61
25. Vejdelek Z.J., Macek K., Budesinsky B. Coll. Czech. Chem. Commun. 22:1955;98-120
26. Kupchan S.M., Eriksen S.P., Liang Y.-T.S. J. Am. Chem. Soc. 88:1966;347-350
27. Bloomfield G.C., Ritchie T.J., Wrigglesworth R. J. Chem. Soc. Perkin Trans. 1. 1992;1229-1236
28. Victory S.F., Appendino G., Vander Velde D.G. Bioorg. Med. Chem. 6:1998;223-229
29. Rocchetti M.T., De Kimpe N. Archivoc. 2003;46-50
30. Brooker L.G.S., White F.L. J. Am. Chem. Soc. 57:1935;2480-2492
31. McElvain S.M., Stevens C.L. J. Am. Chem. Soc. 68:1946;1917-1921
32. McElvain S.M., Kent R.E., Stevens C.L. J. Am. Chem. Soc. 68:1946;1922-1925
33. Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 2nd ed. 1991;Wiley, New York. pp 267-269
34. DeWolfe R.H. Synthesis. 1974;153-172
35. Houben-Weyl. Methoden der Organischen Chemie. 1995;Georg Thieme, Stuttgart. IV Auflage, Bd. E5/1, S. 1-192
36. Kocienski P.J. Protecting Groups. 1994;Georg Thieme, Stuttgart
37. Jarowicki K., Kocienski P.J. J. Chem. Soc. Perkin Trans. 1. 1999;1589-1616
38. Dehmlow E.V., Veretenov A.L. Synthesis. 1992;939-940
39. van Balen H.C.J.G., Broekhuis A.A., Scheeren J.W., Nivard R.J.F. Recl. Trav. Chim. Pays-Bas. 98:1979;36-37