Cryptopleurine, a synthesis based on biogenetic considerations
Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690001309
Abstract
A ten-stage synthesis of (±)-cryptopleurine is described. In line with biogenetic postulates it involves oxidative coupling of 2-(3,4-dihydroxyphenyl)-cis-3-(4-hydroxyphenyl)quinolizidin-4-one (VII; R1= H, R2= O), itself obtained in six steps from 2-methylpyridine, methyl 3,4-dimethoxybenzoate, and 4-methoxyphenylacetyl chloride. The resulting dienone was found to have undergone dehydrogenation and, after rearrangement with acid, methylation, and reduction, afforded the alkaloid (I; R1= R2= R3= H; n= 2).
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Journal Name：Journal of the Chemical Society C: Organic
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CAS no.: 89640-58-4
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