- Production Ways of Plaunotol
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Plaunotol (CAS NO.: ), with its systematic name of 2,6,10,14-Hexadecatetraen-1-ol, 7-(hydroxymethyl)-3,11,15-trimethyl-, (E,Z,E)-, could be produced through many synthetic methods.
Following are some of the synthesis routes:
Route one:
5,9-Dimethyl-4,8-decadien-1-yltriphenylphosphonium iodide (I) is condensed with 4-methyl-6-tetrahydropyranyloxy-4-hexenal (II) using butyllithium as condensing agent in THF, followed by reaction with paraformaldehyde and sec-butyl lithiurn in the same solvent.
Route two:
Homogeranyl iodide (III) is condensed with diethyl ethoxycarbony-methylphosphonate (IV) in the presence of NaH in diethoxyethane to produce the phosphorane (V), which by a Wittig condensation with 4-methyl-6-acetoxy-4-hexenal (VI) by means of NaH yields 7-(ethoxycarbonyl)-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol acetate (VII). Finally, this compound is reduced and hydrolyzed by treatment with LiAlH4.
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