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:

Lewis base-promoted hydrosilylation of cyclic malonates: Synthesis of β-substituted aldehydes and γ-substituted amines

[Frost, Christopher G.; Hartley, Benjamin C. Organic Letters, 2007 , vol. 9, # 21 p. 4259 - 4261]

Ruthenium-catalyzed cycloisomerization of cis-3-En-1-ynes to cyclopentadiene and related derivatives through a 1, 5-sigmatropic hydrogen shift of ruthenium- …

[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]

More Articles...