A mild conversion of phenylpropanoid into rare phenylbutanoids: (E)-4- (2′,4′,5′-trimethoxyphenyl)but-1, 3-diene and ( E )-4-(2′,4′,5′- trimethoxyphenyl)but-1-ene occurring in Zingiber cassumunar
IR@IHBT: CSIR-Institute of Himalayan Bioresource Technology, Palampur
View Archive Info| Field | Value | |
| Title |
A mild conversion of phenylpropanoid
into rare phenylbutanoids: (E)-4-
(2′,4′,5′-trimethoxyphenyl)but-1,
3-diene and ( E )-4-(2′,4′,5′-
trimethoxyphenyl)but-1-ene occurring
in Zingiber cassumunar
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| Creator |
Sinha, Arun K
Sharma, A Joshi, B P Singh, N P |
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| Subject |
Natural Product Chemistry
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| 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.
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| Date |
2005
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://ihbt.csircentral.net/24/1/2005_A_mild_conversion.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- (2′,4′,5′-trimethoxyphenyl)but-1, 3-diene and ( E )-4-(2′,4′,5′- trimethoxyphenyl)but-1-ene occurring in Zingiber cassumunar. Natural Product Research, 19 (8). pp. 771-776. |
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| Relation |
http://ihbt.csircentral.net/24/
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