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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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A mild conversion of phenylpropropnoid into rare phenylbutanoids: (E)-4-(2,4,5-trimethoxyphenyl)but-1,3-diene and (E)-4-(2,4,5-trimethozypheny)but-1-ene occuring in Zingiber cassumunar.

(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.[1]

References

  1. A mild conversion of phenylpropropnoid into rare phenylbutanoids: (E)-4-(2,4,5-trimethoxyphenyl)but-1,3-diene and (E)-4-(2,4,5-trimethozypheny)but-1-ene occuring in Zingiber cassumunar. Sinha, A.K., Sharma, A., Joshi, B.P., Singh, N.P. Nat. Prod. Res. (2005) [Pubmed]
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