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Org Lett. 2005 Jun 9;7(12):2301-4.

Reductive coupling of terpenic allylic halides catalyzed by Cp2TiCl: a short and efficient asymmetric synthesis of onocerane triterpenes.

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  • 1Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avenida Fuentenueva, 18071 Granada, Spain. afbarre@goliat.ugr.es

Abstract

[reaction: see text] Titanocene chloride catalyzes the regioselective alpha,alpha'-homocoupling of terpenic allylic halides. This process has been employed in the short and effective synthesis of terpenoids such as beta-onoceradiene (1), beta-onocerin (2), and squalene (3). Evidence is presented for eta1-allyltitanium species being involved in the coupling.

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