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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

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Title 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
 
Creator Sinha, Arun K
Sharma, A
Joshi, B P
Singh, N P
 
Subject Natural Product Chemistry
 
Description (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.
 
Date 2005
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://ihbt.csircentral.net/227/1/NPR01.pdf
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.
 
Relation http://ihbt.csircentral.net/227/