Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified RambergľBäcklund reaction
…, Y Zhang, Z Huang, X Cao, K Gao
Index: Li, Yang; Zhang, Yu; Huang, Zhi; Cao, Xiaoping; Gao, Kun Canadian Journal of Chemistry, 2004 , vol. 82, # 5 p. 622 - 630
Full Text: HTML
Citation Number: 14
Abstract
A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a ľ 1n by the recently developed one-flask RambergľBäcklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of ...
Related Articles:
[Frost, Christopher G.; Hartley, Benjamin C. Organic Letters, 2007 , vol. 9, # 21 p. 4259 - 4261]
[Datta, Swarup; Odedra, Arjan; Liu, Rai-Shung Journal of the American Chemical Society, 2005 , vol. 127, # 33 p. 11606 - 11607]
Three-component synthesis of (E)-α, β-unsaturated amides of the piperine family
[Schobert; Siegfried; Gordon Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 19 p. 2393 - 2397]