A new approach to (±)-heritonin. The preparation of β-tetralones from allylsilanes and acid chlorides

Tetrahedron Letters

Volumn 45, Issue 21, 2004, Pages 4077-4080

  Silveira, Claudio C ^a   Machado, Alessandra ^a   Braga, Antonio L ^a   Lenardão, Eder João ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

Author keywords

2 Tetralones; Heritonin; Natural products; Selenocarbenium ions

Indexed keywords

ACID; ARYLACETIC ACID DERIVATIVE; BUTENOLIDE; CARBENOID; HERITONIN; NATURAL PRODUCT; SELENOCARBENIUM ION; SESQUITERPENE DERIVATIVE; SILANE DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HERITIERA LITTORALIS; ISOLATION PROCEDURE; MANGROVE; REACTION ANALYSIS; SYNTHESIS; TECHNIQUE;

HERITIERA; HERITIERA LITTORALIS;

EID: 2342513585     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.154     Document Type: Article

References (30)

1. Miles D.H., Lho D.S., de la Cruz A.A., Gomez E.D., Weeks J.A., Atwood J.L. J. Org. Chem. 52:1987;2930
2. Miles D.H., Chitttawong A., Ly V., de Ia Cruz A.A., Gomez E.D. J. Nat. Prod. 52:1989;896
3. Luitgards-Moura J.F., Bermudez E.G.C., Rocha A.F.I., Tsouris P., Rosa-Freitas M.G. Mem. Inst. Oswaldo Cruz. 97:2002;737
4. Irie H., Matsumoto R., Nishimura M., Zhang Y. Chem. Pharm. Bull. 38:1990;1852
5. Ayyangar R.N., Chavan P.S., Zubaidha K.P., Racherla S.U. Tetrahedron. 47:1991;5759
6. Chavan P.S., Zubaidha K.P., Govande C.A., Rao T.S.Y. J. Chem. Soc., Chem. Commun. 1994;1101
7. Subhash P., Chavan S.P., Govande C.A. Green Chem. 4:2002;194
8. Silveira C.C., Lenardo E.J., Araujo M.A., Braga A.L., Dabdoub M.J. Synthesis. 1995;1305
9. Silveira C.C., Machado A., Fiorin G.L., Braga A.L., Dabdoub M.J. Tetrahedron Lett. 37:1996;9173
10. Silveira C.C., Bernardi C.R., Braga A.L., Kaufman T.S. Tetrahedron Lett. 40:1999;4969
11. Silveira C.C., Bernardi C.R., Braga A.L., Kaufman T.S. Tetrahedron Lett. 42:2001;8947
12. Silveira C.C., Bernardi C.R., Braga A.L., Kaufman T.S. Tetrahedron Lett. 44:2003;6137
13. Craig J.C., Torkelson S.M., Findell P.R., Weiner R.L. J. Med. Chem. 32:1989;961
14. Hacksell U., Johanson A.M., Arvidsson L.E., Nilsson J.L.G., Hjorth S., Carlsson A., Wikstrm H., Sanchez D., Lindberg P.J. J. Med. Chem. 27:1984;1003
15. Kanao M., Hashizume Y., Ichikawa K., Irie K., Isoda S. J. Med. Chem. 25:1982;1358
16. For a review on 1, 2-carbonyl transposition, see: Kane V.V., Singh V., Martin A. Tetrahedron. 39:1983;345
17. Shishido K., Goto K., Miyoshi S., Takaishi Y., Shibuya M. J. Org. Chem. 59:1994;406
18. Johansson A.M., Mellin C., Hacksell U. J. Org. Chem. 51:1986;5252
19. Covarrubias-Ziga A., Cant F., Maldonado L.A. J. Org. Chem. 63:1998;2918
20. Oikawa Y., Yonemitsu O. J. Org. Chem. 41:1976;1118
21. Cannon J.G., Lee T., Goldman H.D., Costall B., Naylor R. J. Med. Chem. 20:1977;1111
22. Kanao M., Hashizume Y., Ichikawa K., Irie K., Isoda S. J. Med. Chem. 25:1982;1358
23. Nevy J.B., Hawkinson D.C., Grzegorz B., Yao X., Pollack R.M. J. Am. Chem. Soc. 119:1997;12722
24. Meyers A.I., Henry S.S., Pryde D.C. Tetrahedron Lett. 37:1996;3243
25. 2: C, 76.44, H, 7.90; found: C, 76.20, H, 7.72
26. 4) and concentrated under reduced pressure, to afford a dark oil. Chromatography (hexane/EtOAc, 90:10), gave a 2:1 mixture of β-tetralone 5 and its isomer 15a (80 mg, 41%). Recrystallization (petroleum ether) furnished pure 5 (50 mg, 25%)
27. Burckhalter J.H., Campbell J.R. J. Org. Chem. 26:1961;4232
28. Gray A.D., Smith T.P. J. Org. Chem. 66:2001;7113
29. Colouge J., Chambion J. C. R. 224:1947;128
30. -1): 2926, 1699, 1609, 1502, 1464, 1255, 1126, 1033