Intramolecular cyclization of nerol and the related attack of (Z)-allylic alcohol moiety on the terminal olefin linkage as induced by TiCl4-PhNHMe complex. Synthesis of …

A Itoh, T Saito, K Oshima, H Nozaki

Index: Itoh, Akira; Saito, Tadashi; Oshima, Koichiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 5 p. 1456 - 1459

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Citation Number: 18

Abstract

Nerol was cyclized to terpinyl chloride or bromide in the presence of TiX 4–PhNHMe (1: 1) complex (I, X= Cl, Br) in dichloromethane at− 23° C, geraniol being converted into geranyl halide by simple halogenation. Terminally modified derivatives YCH 2 C (Me)= CHCH 2 CH 2 CMe= CHCH 2 OH (Y= SiMe 3, SnBu 3) of (2Z, 6E) configuration were cyclized by treatment with I to afford limonene in high yields and 100% selectivity. Cyclization of (2Z) ...