Intramolecular cyclization of nerol and the related (z)-allylic alcohols by means of TiCl4-PhNHMe complex. Synthesis of nezukone

✍ Scribed by Tadashi Saito; Akira Itoh; Koichiro Oshima; Hitosi Nozaki

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 225 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95450-4

✦ Synopsis

Nero1 is cyclized to terpinyl chloride or bromide in the presence of TiXq-PhNHMe (1:l) complex in dichloromethane at -23 "C, while cyclization of (Z)-allylic alcohols CH2=CR-CH2CH2CMe=CHCH20H (R = H, Me, Cl) produces seven-membered r-7ng products in fair yields.