A highly efficient transformation of cis- to trans-cinnamic acid derivatives by iodine
Cinnamic acid derivatives (CAs), which have proven to be versatile components, are present in abundance in biologically active natural products, and are widely used as intermediates in the manufacture of pharmaceuticals, and chemicals. The presence of cis- and trans-CAs created difficulties for natural product and organic synthetic studies. A highly efficient method that utilized iodine to entirely convert cis- CAs into their trans-forms was developed to solve this problem. The mechanism of study revealed this conversion occurred via an anti-diiodo intermediate.
Studies on the constituents of Viburnum species. On phenolic glycosides from the leaves of Viburnum wrightii MIQ
Four new phenolic glycosides, umbelliferone 6-O-trans-caffeoyl-β-D-glucopyranoside, p-hydroxyphenyl 4-O-transcaffeoyl-β-D-glucopyranoside, p-hydroxyphenyl 2-O-cis-p-coumaroyl-β-D-glucopyranoside and p-hydroxyphenyl 6-O-cis-p-coumaroyl-β-D-glucopyranoside, and five known compounds were isolated from the leaves of Viburnum wrightii MIQ.
Machida,Kikuchi
p. 248 - 251
(2007/10/02)
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