Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity

Cini, Melchior; Bradshaw, Tracey D.; Lewis, William; Woodward, Simon

Abstract

The copper-catalysed (10 mol-% CuBr·SMe2, CuCN·LiCl or CuI/PPh3) addition of RMgBr to the pentafulvene 1-(cyclopenta-2,4-dien-1-ylidenemethyl)-2-methoxybenzene allows the formation of cyclopentadienyl derivatives with α-CHR(2-MeOPh) sidechains (R = Me, Et, nBu, iBu, allyl, Ph) without H– transfer. The deprotonation of these sec-alkyl-substituted cyclopentadienyls followed by the addition of TiCl4 allows the isolation of TiCl2{η5-C5H4CHR(2-OMePh)} as rac/meso mixtures that show activity against human colon, breast and pancreatic cell lines (GI50 2.3–42.4 μM).

Citation

Cini, M., Bradshaw, T. D., Lewis, W., & Woodward, S. (2013). Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity. European Journal of Organic Chemistry, 2013(19),

• Journal Article Type: Article
• Online Publication Date: May 15, 2013
• Publication Date: Jun 19, 2013
• Deposit Date: Jun 24, 2014
• Publicly Available Date: Jun 24, 2014
• Journal: European Journal of Organic Chemistry
• Print ISSN: 1434-193X
• Electronic ISSN: 1099-0690
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 2013
• Issue: 19
• Public URL: https://nottingham-repository.worktribe.com/output/715614
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300474/abstract
• Related Public URLs: http://www.interscience.wiley.com/
• Contract Date: Jun 24, 2014