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Communication | Special issue | Vol 82, No. 1, 2010, pp.249-255
Published online, 25th January, 2010
DOI: 10.3987/COM-09-S(E)1
Nucleophilic Phosphine-Catalyzed Iodocyclization of Isoprenoids Bearing an Oxygen Terminal Group

Akira Sakakura, Gakujun Shomi, Atsushi Ukai, and Kazuaki Ishihara*

*Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601,

Abstract

The nucleophilic phosphine-catalyzed diastereoselective iodocyclization of linear isoprenoids bearing an oxygen terminal group was investigated. TBDMS ether of homogeraniol and TBDMS ester of homogeranic acid were successfully converted to the corresponding iodopolycyclic products in the presence of a catalytic amount of triphenylphosphine with complete diastereoselectivity.