Tandem addition-cyclization mediated by sulfanyl radicals: a versatile strategy for iridoids synthesis

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 5111-5118

  Sánchez, Elena M ^a   Arteaga, Jesús F ^a   Domingo, Victor ^a   Quílez del Moral, José F ^a   Herrador, M Mar ^a   Barrero, Alejandro F ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

Enantioselective synthesis; Iridanes; Radical cyclizations; Sulfanyl radical

Indexed keywords

CITRONELENE DERIVATIVE; IRIDANE DEHYDROIRIDOMYRMECIN; IRIDOID; LINALOOL; TERPENE; TERPENOID DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 42749087155     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.058     Document Type: Article

References (46)

1. Meinwald J., Jones T.H., Eisner T., and Hicks K. Proc. Natl. Acad. Sci. U.S.A., Early Ed. 74 (1977) 2189-2193
2. Boros C.A., and Stermitz F.R. J. Nat. Prod. 53 (1990) 1055-1147
3. Boros C.A., and Stermitz F.R. J. Nat. Prod. 54 (1991) 1173-1246
4. Nangia A., Prasuna G., and Rao B. Tetrahedron 53 (1997) 14507-14545
5. Dinda B., Debnath S., and Harigaya Y. Chem. Pharm. Bull. 55 (2007) 159-222
6. Franzyk H. Synthetic Aspects of Iridoid Chemistry. In: Kinghorn A.D., Falk H., Kirby G.W., and Herz W. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 79 (2000), Springer, Wien, New York, NY 1-114
7. Piccinini P., Vidari G., and Zanoni G. J. Am. Chem. Soc. 126 (2004) 5088-5089
8. Tanaka H., Kamikubo T., Yoshida N., Sakagami H., Taniguchi T., and Ogasawara K. Org. Lett. 3 (2001) 679-681
9. Korte F., Falbe J., and Zschocke A. Tetrahedron 6 (1959) 201-216
10. Chauhan K.R., Zhang Q.-H., and Aldrich J.R. Tetrahedron Lett. 45 (2004) 3339-3340
11. Schöllhorn B., and Mulzer J. Eur. J. Org. Chem. (2006) 901-908
12. Chatgilialoglu C., and Asmus K.D. Sulfur-centered Reactive Intermediates in Chemistry and Biology (1990), Plenum, New York, NY
13. Wardman P. In: Alfassi Z.B. (Ed). S-Centered Radicals (1999), Wiley, New York, NY Chapter 10
14. Abedinzadeh Z. Can. J. Physiol. Pharmacol. 79 (2001) 166-170
15. Giles G.I., and Jacob C. Biol. Chem. 383 (2002) 375-388
16. For revisions of sulfanyl radicals, see:
17. Griesbaum K. Angew. Chem., Int. Ed. Engl. 9 (1970) 273-287
18. Miyata O., and Naito T. C. R. Acad. Sci., Ser. IIc: Chim. 4 (2001) 401-421
19. Bertrand P., and Ferreri C. Sulfur-Centered Radicals. In: Renaud P., and Sibi P. (Eds). Radicals in Organic Synthesis Vol. 2 (2001), Wiley-VCH, Weinheim 485-504
20. Zard S.Z. In: Compton R.G., Davies S.G., and Evans J. (Eds). Radical Reactions in Organic Synthesis (2003), Oxford University Press
21. Miyata O., Ozawa Y., Ninomiya I., and Naito T. Tetrahedron 56 (2000) 6199-6207
22. Naito T., Honda Y., Bhavakul V., Yamaguchi S., Fujiwara A., Miyata O., and Ninomiya I. Chem. Pharm. Bull. 45 (1997) 1932-1939
23. Miyata O., Nishiguchi A., Inomiya I., Aoe K., Okamura K., and Naito T. J. Org. Chem. 65 (2000) 6922-6931
24. Miyata O., Muroya K., Koide J., and Naito T. Synlett (1998) 271-272
25. Murakami S., Takemoto T., and Shimizu Z. J. Pharm. Soc. Jpn. 73 (1953) 1026-1029
26. Feldman K.S., Romanelli A.L., Ruckle Jr. R.E., and Miller R.F. J. Am. Chem. Soc. 110 (1988) 3300-3302
27. Feldman K.S., and Burns C.B. J. Org. Chem. 56 (1991) 4601-4602
28. Feldman K.S., Ruckle R.E., and Romanelli A.L. Tetrahedron Lett. 30 (1989) 5845-5848
29. Pedrosa R., Andrés C., Duque-Soladana J.P., Maestro A., and Nieto J. Tetrahedron: Asymmetry 14 (2003) 2985-2990
30. Barrero A.F., Arseniyadis S., Herrador M.M., Quílez del Moral J.F., Arteaga J., and Sánchez E.M. Synlett (2005) 591-594
31. Montevecchi P.C., and Navacchia M.L. J. Org. Chem. 62 (1997) 5600-5607
32. Walling C., and Helmreich W. J. Am. Chem. Soc. 81 (1959) 1144-1148
33. Asscher M., and Vofsi D. J. Chem. Soc. (1964) 4962-4971
34. Sinnreich J., and Asscher M. J Chem. Soc., Perkin Trans. 1 (1971) 1543-1545
35. The ratio of stereoisomers obtained was determined by HPLC.
36. Beckwith A.L.J., and Schiesser C.H. Tetrahedron Lett. 26 (1985) 373-376
37. Beckwith A.L.J., and Schiesser C.H. Tetrahedron 41 (1985) 3925-3941
38. Spellmeyer D.C., and Houk K.N. J. Org. Chem. 52 (1987) 959-974
39. Beckwith A.L.J., and Zimmermann J. J. Org. Chem. 56 (1991) 5791-5796
40. The conformational or steric energy the methyl group is 1.74 kcal/mol, whereas that of the acetate is 0.79 kcal/mol. Eliel E.L., Wilen S.H., and Mander L.N. Stereochemistry of Organic Compounds (1994), John Wiley and Sons, New York, NY
41. Giese B. Stereoselectivity of Radical Reactions. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vol. 1 (2001), Wiley-VCH, Weinheim 380-399
42. Rosenkranz G., Kaufmann S.T., and Romo J. J. Am. Chem. Soc. 71 (1949) 3689-3694
43. Sakai T., Nakajima K., and Sakan T. Bull. Chem. Soc. Jpn. 53 (1980) 3683-3686
44. Boulin B., Arreguy-San Miguel B., and Delmond B. Tetrahedron 56 (2000) 3927-3932
45. De Lucchi O., Miotti U., and Modena G. Org. React. 40 (1991) 157-405
46. Hagiwara H., Kobayashi T., Suzuki T., and Ando M. Tetrahedron 57 (2001) 5039-5043