A Short Route to Dihydrocapsaicinoids

Harumi Kaga; Masakatsu Miura; Kazuhiko Orito

doi:10.1055/s-1989-27414

Synthesis 1989; 1989(11): 864-866
DOI: 10.1055/s-1989-27414

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A Short Route to Dihydrocapsaicinoids

Harumi Kaga^* , Masakatsu Miura, Kazuhiko Orito

^*Government Industrial Development Laboratory, Hokkaido, Sapporo, Hokkaido 004, Japan

Abstract

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Huang-Minlon reduction of 8-methyl-7-oxononanoic acid (4ba), obtained by the acylation of cyclohexanone enamine 2a with 2-methylpropanoyl chloride (1b) followed by ring cleavage of the resultant ß-diketone 3ba affords 8-methylnonanoic acid (5ba), the chloride of which reacts readily with 4-hydroxy-3-methoxybenzylamine to give dihydrocapsaicin (7ba). This reaction sequence works also efficiently for other dihydrocapsaicinoids such as 7aa and 7bb.

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