Polyfunctionalized cyclopentanes vis 5-exo-trig tributyltin hydride mediated free radical cyclization of δ-functionalized tethered acetylenic derivatives from sugars

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6749-6750

  Marco Contelles, José ^a   Rodríguez, Mercedes ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; FREE RADICAL; HYDRAZONE DERIVATIVE; IMINE; RIBOSE; TRIBUTYLTIN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRECURSOR; SYNTHESIS;

EID: 0032505234     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01416-6     Document Type: Article

References (11)

1. 1. Martínez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155.
2. 2. Marco-Contelles, J.; Destabel, C.; Gallego, P.; Chiara, J. L.; Bernabé, M. J. Org. Chem. 1996, 61, 1354.
3. 3. For an excellent review of free radical cyclizations onto C-N multiple bonds, see: Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
4. 4. a) For the cyclization of alkynyl-tethered mesitylsulfonylhydrazones, see: Kim, S.; Cho, J. R. Kim, S.; Cho, J. R. Synlett, 1992, 629;
5. b) For the cyclization of alkynyl-tethered N-aziridinyl imines, see: Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882.
6. 5. For free radical chemistry of imines: Tomaszewski, M. J.; Warkentin, J.; Werstiuk, N. H. Aust. J. Chem. 1995, 48, 291.
7. 6. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
8. 7. a) Tiecco, M.; Testaferri, L.; Marini, F.; Santi, C.; Bagnoli, L.; Temperini, A. Tetrahdron Lett. 1997, 53, 7311;
9. b) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron Lett. 1994, 35, 6369.
10. 3B (1 equiv). After 18 h the solvent was removed and the residue was dissolved in ethyl ether and 15% aqueous solution of KF, and stirred for 2 h. The organic phase was separarted, dried, filtered and evaporated. The crude material was submitted to flash chromatography eluting with hexane/ethyl acetate mixtures to give product 3 (346 mg, 62% yield).
11. 9. Details of the synthetic sequences leading to these radical precursors will be described elsewhere.