Synthesis of azaspiro[4.5]decane systems by oxidative cyclization of olefinic precursors

Tetrahedron

Volumn 54, Issue 40, 1998, Pages 12379-12388

  Martín López, María J ^a   Bermejo, Francisco ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Alkaloids; Amino acids and derivatives; Lactams; Lactones; Spiro compounds

Indexed keywords

6 BENZYL 3 METHYL 1,6 DIAZASPIRO[4.5]DEC 3 ENE 2,7 DIONE; 6 BENZYLOXYCARBONYL 1 OXA 6 AZASPIRO[4.5]DECAN 2 ONE; 6 BENZYLOXYCARBONYL 1,6 DIAZASPIRO[4.5]DECAN 2 ONE; ALKALOID; ALKANE DERIVATIVE; ALKENE; AZASPIRO[4.5]DECANE; BENZYL DERIVATIVE; DECANE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR INTERACTION; OXIDATION; POSTSYNAPTIC INHIBITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032191826     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00746-7     Document Type: Article

References (30)

1. [1] Tokuyama T, Uenoyama K, Brown G, Daly JW, Witkop B. Helv. Chim. Acta, 1974; 57: 2597
2. [2] Inubushi Y, Ibuka T. Heterocycles, 1977; 8: 633
3. [3] Daly JW, Brown AB, Mensah-Dwumah M, Meyers CW. Toxicon, 1978; 16: 163.
4. [4] Spivak CE, Maleque MA, Oliviera AC, Masukawa L, Tokuyama K, Daly JW, Albuquerque EX. Mol. Pharmacol., 1982; 21: 351.
5. [5] Takahashi K, Witkop B, Brossi A, Maleque MA, Albuquerque, EX. Helv. Chim. Acta, 1982; 65: 252-261.
6. [6] Elliot J, Raftery, MA. Biochem. and Biophys. Res. Commun., 1977; 77: 1347.
7. [7] Albuquerque EY, Barnard EP, Chui TH, Lapa AJ, Dolly JO, Jansson S, Daly J, Witkop B. Proc. Natl. Acad. Sci. U.S.A., 1973; 70: 949.
8. [8] Keppens M, De Kimpe N. J. Org. Chem. 1995; 60: 3916-3918.
9. [9] Wanner MJ, Koomen G-J. J. Org. Chem. 1995; 60: 5634-5637.
10. [10] Yamane T, Ogasawara K, Synlett, 1996; 925.
11. [11] Chou T, Kuramoto M, Otani Y, Shikano M, Yazawa K, Uemura D. Tetrahedron Lett., 1996; 37: 3871-3874.
12. [12] Nonato MG, Garson MJ, Truscott JW, Carver JA. Phytochemistry, 1993; 34: 1159-1163.
13. [13] Buttery RG, Juliano BO, Ling LC. Chem & Ind., 1983; 478.
14. [14] Byrne LT, Guevara BQ, Patalinghugh WC, Recio BV, Ualat CR, White AH. Aust. J. Chem., 1992; 45: 1903-1908.
15. [15] Martin-Löpez MJ, Bermejo-González F. Tetrahedron Lett., 1994; 35: 4235-4238.
16. [16] Martin MJ, Bermejo F. Tetrahedron Lett., 1995; 36: 7705-7708.
17. [17] Martin-López MJ, Bermejo-González F. Tetrahedron Lett., 1994; 35: 8843-8846.
18. [18] Rodríguez R, Bermejo F. Tetrahedron Lett., 1996; 37: 5581-5584.
19. [19] Knapp S, Levorse AT. J. Org. Chem., 1988; 53: 4006.
20. [20] Rico R, Bermejo F. Tetrahedron Lett., 1996; 37: 5809-5812.
21. [21] Stereoselective methods to prepare 4-ylidenebutenolides are well known in the literature; see, for example: Corrie JET. Tetrahedron Lett, 1971; 12: 4873-4876 and the three following references.
22. [22] Howe RK. J. Org. Chem., 1973; 38: 4164-4617.
23. [23] Ingham CF, Massy-Westropp RA, Reynolds GD. Aust. J. Chem., 1974; 27: 1477-1489.
24. [24] Knight DW, Pattenden GF. J. Chem. Soc. Perkin I., 1975, 635-644.
25. [25] Kimura Y, Nakajima H, Hamasaki T, Matsumoto T, Matsuda Y, Tsuneda A. Agric. Biol. Chem., 1990; 54: 813-814.
26. [26] Bartlett PA. Olefin cyclization processes that form carbon-heteroatom bonds. In: Asymmetric Synthesis Morrison JD, editor. New York: Academic Press, 1984: 411-454.
27. [27] Schoemaker HE, Speckamp WN Tetrahedron Lett., 1978; 19: 1515-1518.
28. [28] Schoemaker HE, Speckamp WN Tetrahedron Lett., 1978; 19: 4841-4844.
29. [29] Evans DA, Thomas EW. Tetrahedron Lett., 1979; 20: 411-414.
30. [30] Still WC, Kahn MA. J. Org. Chem., 1978; 43: 2923-2925.