Regioselective reduction of the α, β - double bond of some naturally occurring dienamides using NaBH4/I2 system

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 677-678

  Das, Biswanath ^a   Kashinatham, A ^a   Madhusudhan, P ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; IODINE; NATURAL PRODUCT; PIPERINE; SODIUM BOROHYDRIDE;

ARTICLE; CHEMICAL BOND; REDUCTION; STEREOSPECIFICITY;

EID: 0032509934     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10590-1     Document Type: Article

References (13)

1. 1 Part IV in the series "Synthetic Studies on Natural Products"; for Part III, see Das, B.; Madhusudhan, P. and Kashinatham, A. J. Chem. Research (S), 1997 (submitted). IICT Communication No. 3912.
2. 2 Banerji, A. J. Ind. Chem. Soc., 1991, 69, 53.
3. 3 Kiuchi, F.; Nakamura, N.; Tsuda, Y.; Kondo, K. and Yoshimura, H. Chem. Pharm. Bull., 1988, 36, 2452.
4. 4 Duh, C.-Y.; Wu, Y.-C. and Wang, S.-K. J. Nat. Prod. 1990, 53, 1575.
5. 5 Rao, A. B.; Rao, M.V.; Kumar, A.; Krupadanam, G.L.D. and Srimannarayana, G. Tetrahedron Lett., 1994, 35, 279.
6. 6 Das, B.; Kashinatham, A. and Madhusudhan, P. Tetrahedron Lett. 1997 (Accepted).
7. 7 Das, B.; Kashinatham, A. and Srinivas, K.V.N.S. Planta Med. 1996, 62, 582.
8. 2 atmosphere. After 20 min. the reaction mixture was quenched with MeOH till the effervescence was ceased. Evaporation of the solvent followed by purification of the crude product by column chromatography over silica gel afforded dihydropiperine 4 (0.42g, 74%).
9. 2 (0.76g, 0.003 mole) under above conditions two reaction products, tetrahydropiperine 7 (0.33g, 58%) and dihydropiperine 4 (0.08g, 14%) were obtained.
10. +.,5), 149 (12), 135 (18), 98 (100).
11. +., 45), 204 (18), 135 (48), 127 (100).
12. 10 Narayana, C. and Periasamy, M. J. Organomet. Chem. 1987, 323, 145.
13. 11 Bhanuprasad, A.S.; Bhaskar Kanth, J.V. and Periasamy, M. Tetrahedron 1992, 45, 4623.