A Facile Synthesis of 3,4-Dienamides by the Reaction of Propargyl Alcohols with Cyclic Amide Acetals and Their Stereoselective Rearrangement to 2(E),4(Z)-Dienamides Promoted with Alumina. Total Synthesis of Isochavicine

DOI: 10.1021/jo00181a012

Source and publish data:

Journal of Organic Chemistry p. 1204 - 1208 (1984)

Update date:2022-08-03

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Authors:

Tsuboi, Sadao

Nooda, Yuji

Takeda, Akira

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Article abstract of DOI:10.1021/jo00181a012

Thermal condensation of propargyl alcohols with acetals of 1-acetylpyrrolidine and 1-acetylpiperidine gave 3,4-dienamides in good yields.Alumina promoted the rearrangement of β-allenic amides to 2(E),4(Z)-dienamides stereoselectively.Its application to the synthesis of isochavicine of pepper components is described.Carbon-13 NMR data of these dienamides were obtained.

Full text of DOI:10.1021/jo00181a012

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