A. Sinha, A. Sharma, B. Joshi
Dec 1, 2005
Citations
0
Influential Citations
4
Citations
Journal
Natural Product Research
Abstract
(E)-4-(2′,4′,5′-trimethoxyphenyl)but-1,3-diene (4) and (E)-4-(2′,4′,5′-trimethoxyphenyl)but-1-ene (6), bioactive phenylbutanoids of Zingiber cassumunar, were synthesized exclusively with trans geometry. Treatment of methylmagnesium iodide with (E)-2,4,5-trimethoxycinnamaldehyde (2), an oxidized product of abundantly available toxic (Z)-phenylpropanoid (1) of Acorus calamus, gave (E)-4-(2′,4′,5′-trimethoxyphenyl)but-3-en-2-ol (3) which upon dehydration with copper sulphate/silica gel under microwave irradiation for 3 min afforded 4 in 58% yield. Further, catalytic hydrogenation of 4 with 10% Pd/C afforded 4-(2′,4′,5′-trimethoxyphenyl)butane (5) which upon dehydrogenation with DDQ/SiO2 afforded hypolipidemic 6 in 54% yield.