Total synthesis of (.+-.)-chelidonine

M Cushman, TC Choong, JT Valko…

Index: Cushman, Mark; Choong, Tung-Chung; Valko, Joseph T.; Koleck, Mary P. Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5067 - 5073

Full Text: HTML

Citation Number: 86

Abstract

Condensation of the Schiff base 8 with 3, 4-(methy1enedioxy) homophthalic anhydride (13) was exploited as the key step in a total synthesis of the benzophenanthridine alkaloid (*)- chelidonine (1). A variety of reaction conditions were investigated in order to maximize the production of the desired thermodynamically less stable cis diastereomer. A method was devised for the conversion of 24 to its acid chloride without production of the indeno [l, 2-c] ...

Related Articles:

Synthesis, anti-GABA activity and preferred conformation of bicuculline and norbicuculline enantiomers

[Kardos; Blandl; Luyen; Doernyei; Gacs-Baitz; Simonyi; Cash; Blasko; Szantay European Journal of Medicinal Chemistry, 1996 , vol. 31, # 10 p. 761 - 765]

Directed ortho metalation of n, n-diethyl benzamides. Methodology and regiospecific synthesis of useful contiguously tri-and tetra-substituted oxygenated aromatics, …

[De Silva; Reed; Billedeau; Wang; Norris; Snieckus Tetrahedron, 1992 , vol. 48, # 23 p. 4863 - 4878]

Directed ortho metalation of n, n-diethyl benzamides. Methodology and regiospecific synthesis of useful contiguously tri-and tetra-substituted oxygenated aromatics, …

[De Silva; Reed; Billedeau; Wang; Norris; Snieckus Tetrahedron, 1992 , vol. 48, # 23 p. 4863 - 4878]

More Articles...