Tetrahedron letters

Anodic cyanation of C-4 hydroxylated piperidines: total synthesis of (±)-alkaloid 241D

N Girard, JP Hurvois

Index: Girard, Nicolas; Hurvois, Jean-Pierre Tetrahedron Letters, 2007 , vol. 48, # 23 p. 4097 - 4099

Full Text: HTML

Citation Number: 23

Abstract

A stereospecific synthesis of dendrobates (±)-alkaloid 241D is described. Key steps in this approach involved the stepwise electrochemical synthesis of C-4 substituted α-aminonitriles and their alkylation with iodomethane and 1-bromononane, respectively. The N-aryl group was removed in the last step through a Birch dearomatization followed by the hydrolysis of the intermediate dienamines.

Related Articles:

Ruthenium-catalyzed cytochrome P-450 type oxidation of tertiary amines with alkyl hydroperoxides

[Murahashi, Shun-Ichi; Naota, Takeshi; Yonemura, Koichi Journal of the American Chemical Society, 1988 , vol. 110, # 24 p. 8256 - 8258]

Ruthenium-catalyzed cytochrome P-450 type oxidation of tertiary amines with alkyl hydroperoxides

[Murahashi, Shun-Ichi; Naota, Takeshi; Yonemura, Koichi Journal of the American Chemical Society, 1988 , vol. 110, # 24 p. 8256 - 8258]

… observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides

[Lloyd, Wayne; Reese, Colin B.; Song, Quanlai; Vandersteen, Anthony M.; Visintin, Cristina; Zhang, Pei-Zhou Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 2 p. 165 - 176]

More Articles...