Bulletin of the Chemical Society of Japan p. 1456 - 1459 (1981)
Update date:2022-07-29
Topics:
Itoh, Akira
Saito, Tadashi
Oshima, Koichiro
Nozaki, Hitosi
Nerol was cyclized to terpinyl chloride or bromide in the presence of TiX4-PhNHMe (1:1) complex (I, X=Cl, Br) in dichloromethane at -23 deg C, geraniol being converted into geranyl halide by simple halogenation.Terminally modified derivatives YCH2C(Me)=CHCH2CH2CMe=CHCH2OH (Y=SiMe3, SnBu3) of (2Z,6E) configuration were cyclized by treatment with I to afford limonene in high yields and 100percent selectivity.Cyclization of (2Z) isomers of CH2=CR-CH2CH2CMe=CHCH2OH (R=H, Me, Cl) produced seven-membered carbocyclic products in fair yields.The novel procedure has been utilized in the synthesis of nezukone from (2E)-3-isopropyl-2,6-heptadien-1-ol involving five steps.
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(1981)