Sinha, Arun K and Sharma, A and Joshi, B P and Singh, N P (2005) A mild conversion of phenylpropanoid into rare phenylbutanoids: (E)-4-(20,40,50-trimethoxyphenyl)but-1, 3-diene and (E)-4-(20,40,50-trimethoxyphenyl)but-1-ene occurring in Zingiber cassumunar. Natural Product Research, 19 (8). pp. 771-776.

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(E)-4-(20,40,50-trimethoxyphenyl)but-1,3-diene (4) and (E)-4-(20,40,50-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-(20,40,50-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-(20,40,50-trimethoxyphenyl) butane (5) which upon dehydrogenation with DDQ/SiO2 afforded hypolipidemic 6 in 54% yield.

Item Type: Article
Uncontrolled Keywords: Zingiber cassumunar; Acorus calamus; Phenylbutanoids; Phenylpropanoid; Microwave technique; DDQ
Subjects: Natural Product Chemistry
Depositing User: Dr. Aparna Maitra Pati
Date Deposited: 29 Dec 2011 10:15
Last Modified: 29 Dec 2011 10:15

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