To obtain the subject new compound used as an intermediate for synthesizing plaunotol useful as an antitumor agent.
An allyl halide compound of formula I (A is a hydroxyl group- protecting group; X is a halogen). For example, (E, Z, E, E)-1-benzyloxy-7- benzyloxymethyl-16-chloro-3,11,15-trimethyl-2,6,10,14-hexadecatetraene. The compound of formula I is obtained by reacting a compound of formula II with 1-10 mole equivalents of 2-methyl-3,3-dialkoxy-1-butene in the presence of an acid catalyst (preferably 0.01-10 wt.% of pyridinium p-toluenesulfonate) at 50-150°C for 1-5 hr, twice performing a 5-carbon-elongating reaction comprising reducing the carbonyl group of the obtained compound and subsequently halogenating the obtained secondary allyl alcohol of formula III.
UJITA KATSUJI
TORIHARA MASAHIRO
KANEHIRA KOICHI
TAMAI HIRONOBU
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